JP7315419B2 - Organic EL display device - Google Patents

Description

The present invention relates to an organic EL display device.

In recent years, in electronic devices such as mobile phones and personal digital assistants, the development and mass production of display devices using organic EL (organic electroluminescence), which is a self-luminous element, is progressing in order to meet the demand for further thinning and lightening and curved surface display, which has been difficult for current mainstream liquid crystal display devices. Among them, in order to take advantage of the features of thinness and lightness, application to high-definition and small displays (hereinafter referred to as microdisplays) of about 0.5 inches, such as head-mounted displays and electronic viewfinders, is expected.

There are two major display methods for organic EL displays: a method in which a white light-emitting layer is formed and color filters are used to express colors such as RGB, and a method in which light-emitting layers that emit respective colors such as RGB are vapor-deposited to express colors. Since microdisplays have fine pixels, it is very difficult to selectively form RGB light-emitting layers. Therefore, the method of using a color filter for the white light emitting layer is actively adopted for the microdisplay.

As mentioned above, the pixel size of a microdisplay is as small as 1 μm to 5 μm. Therefore, the conventional method of fabricating organic EL elements and color filters on separate substrates and bonding them together results in reduced accuracy and color shifts. Therefore, a method of forming a color filter on an organic EL element has been proposed.

Color filters can be manufactured by an inkjet method, a photolithography method, or the like, but the photolithography method, which enables the formation of fine pixels, is being adopted. However, since the organic light-emitting layer has low heat resistance, it needs to be baked at a low temperature in order to form a color filter on the organic EL element. Specifically, in the conventional photolithography method, baking is performed at a very high temperature of 230° C., but baking at about 100° C. is required. However, if the baking temperature of the colored pixels is lowered, curing becomes insufficient, and problems such as peeling and surface roughness of the colored pixels due to the solvent contained in the applied coloring composition occur during pixel formation in the next step. On the other hand, when the exposure dose is increased, the reaction of the crosslinkable component contained in the colored pixels progresses and curing progresses, but it is very difficult to form pixels of any size.

In order to solve the above problems, for example, Patent Document 1 proposes a method of increasing curability at low temperature by using an alkali-soluble resin containing an epoxy group and a coloring composition containing an amine compound as a curing agent. However, the addition of an amine compound to the coloring composition may reduce the transmittance of the color filter. Further, Patent Document 2 proposes a method of curing at a low temperature by using an oxetane compound and a benzophenone-based compound having a peroxide skeleton as a thermal polymerization initiator.

JP 2012-063745 A JP-A-2003-255531

However, in Patent Documents 1 and 2 described above, the curing temperature is 150° C. Considering the heat resistance of the organic EL element, further low-temperature curability is required. In addition, in order to achieve high color reproducibility with a thin film, it is necessary to increase the colorant concentration of the color filter. With the methods of Patent Documents 1 and 2, it is very difficult to obtain sufficient sensitivity for patterning when the coloring material density is high.

SUMMARY OF THE INVENTION In view of the above problems, it is an object of the present invention to provide a high-quality organic EL display device having high luminance and high color reproducibility.

That is, the organic EL display device according to the present invention is an organic EL display device having an organic EL layer and a color filter on a silicon substrate on which driving elements are formed,
the color filter has pixels including red pixels, green pixels, and blue pixels;
The film thickness of the pixel is in the range of 1.0 μm to 2.0 μm,
In the spectral transmittance of the red pixel, the maximum transmittance of light in the wavelength range of 450 nm to 560 nm is 0.4% or less, and the transmittance of light in the wavelength range of 600 nm to 700 nm is 80% or more and less than 100%;
The spectral transmittance of the green pixel has a maximum transmittance of 2% or less for light in the wavelength range of 400 nm to 470 nm, a transmittance of 70% or more for light with a wavelength of 520 nm, and a transmittance of 60% or less for light with a wavelength of 550 nm,
The spectral transmittance of the blue pixel has a maximum light transmittance of less than 20% in a wavelength range of 500 nm to 560 nm,
The pixel contains a coloring agent (A), a photopolymerizable monomer (B), a photopolymerization initiator (C), and a resin (D), and the photopolymerization monomer (B) is a cured product of a photosensitive coloring composition containing a compound represented by the following general formula (1) and a photopolymerization initiator (C) containing an oxime ester photopolymerization initiator.
General formula (1)
[ _CH2 =CHC(=O)-( _OCmH2m ) _{n -OCH2 ] 3 - CCH2CH3}
(In general formula (1), m represents an integer of 1 to 3, n represents an integer of 0 to 2, and multiple m and n may be the same or different.)

In one embodiment of the organic EL device of the present invention, the content of the compound represented by the general formula (1) is 50% by mass or more relative to the total amount of the photopolymerizable monomer (B).

In one embodiment of the organic EL device of the present invention, the oxime ester photopolymerization initiator is a compound represented by the following general formula (2).

（一般式（２）中、Ｚは直接結合、又は－Ｃ（＝Ｏ）－基を表し、Ｒ^１は置換基を有してもよい炭素数１～２０のアルキル基を表し、Ｒ^２は置換基を有してもよい炭素数１～２０のアルキル基、又は置換基を有してもよいアリール基を表し、Ｒ^３～Ｒ^１０はそれぞれ独立して、水素原子、置換基を有してもよい炭素数１～２０のアルキル基、置換基を有してもよいアリール基、ニトロ基、又はＲ^１１－Ｃ（＝Ｏ）－基を表す。Ｒ^１１は置換基を有してもよいアリール基を表す。）

(In general formula (2), Z represents a direct bond or a -C(=O)- group, R ¹ represents an optionally substituted C 1-20 alkyl group, R ² represents an optionally substituted C 1-20 alkyl group or an optionally substituted aryl group, and R ³ to R ¹⁰ each independently represents a hydrogen atom, an optionally substituted C 1-20 alkyl group, an optionally substituted aryl group, or a nitro group. , or represents an R ¹¹ -C(=O)- group.R ¹¹ represents an aryl group which may have a substituent.)

In one embodiment of the organic EL device of the present invention, the resin (D) contains a photosensitive resin.

In one embodiment of the organic EL device of the present invention, the photosensitive resin is
In the presence of the reaction product of the hydroxyl group of the compound (a) having two hydroxyl groups and one thiol group in the molecule and the acid anhydride group of pyromellitic anhydride and/or trimellitic anhydride, the hydroxyl group of a hydroxyl group-containing polymer obtained by polymerizing the ethylenically unsaturated monomer (c) containing the hydroxyl group-containing ethylenically unsaturated monomer (b), and the compound (d) having one isocyanate group and one or more (meth)acryloyl groups. Is a resin reacted with an isocyanate group,
The content of structural units derived from the hydroxyl-containing ethylenically unsaturated monomer (b) is 35% by mass or more and 80% by mass or less with respect to the total amount of structural units derived from the ethylenically unsaturated monomer (c). Contains a photosensitive resin (E).

One embodiment of the organic EL device of the present invention is
the content of the coloring agent (A) in the red pixel is 24% by mass or more and 67% by mass or less;
The content of the coloring agent (A) in the green pixel is 30% by mass or more and 55% by mass or less, and
The content of the coloring agent (A) in the blue pixel is 30% by mass or more and 47% by mass.

According to the present invention, it is possible to provide a high-quality organic EL display device having high luminance and high color reproducibility.

FIG. 1 is a schematic cross-sectional view of the organic EL display device of this embodiment.

Embodiments of the present invention will be described in detail below.
In this specification, the terms "(meth)acryloyl", "(meth)acryl", "(meth)acrylic acid", "(meth)acrylate", or "(meth)acrylamide" refer to "acryloyl and/or methacryloyl", "acrylic and/or methacryl", "acrylic acid and/or methacrylic acid", "acrylate and/or methacrylate", or "acrylamide and/or methacrylamide", respectively, unless otherwise specified. . Moreover, "C.I." mentioned in this specification means a color index (C.I.).

The organic EL display device of the present embodiment is an organic EL display device having an organic EL layer and a color filter on a silicon substrate on which driving elements are formed,
the color filter has pixels including red pixels, green pixels, and blue pixels;
The film thickness of the pixel is in the range of 1.0 μm to 2.0 μm,
In the spectral transmittance of the red pixel, the maximum transmittance of light in the wavelength range of 450 nm to 560 nm is 0.4% or less, and the transmittance of light in the wavelength range of 600 nm to 700 nm is 80% or more and less than 100%;
The spectral transmittance of the green pixel has a maximum transmittance of 2% or less for light in the wavelength range of 400 nm to 470 nm, a transmittance of 70% or more for light with a wavelength of 520 nm, and a transmittance of 60% or less for light with a wavelength of 550 nm,
The spectral transmittance of the blue pixel has a maximum light transmittance of less than 20% in a wavelength range of 500 nm to 560 nm,
The pixel contains a coloring agent (A), a photopolymerizable monomer (B), a photopolymerization initiator (C), and a resin (D), and the photopolymerization monomer (B) is a cured product of a photosensitive coloring composition containing a compound represented by the following general formula (1) and a photopolymerization initiator (C) containing an oxime ester photopolymerization initiator.
General formula (1)
[ _CH2 =CHC(=O)-( _OCmH2m ) _{n -OCH2 ] 3 - CCH2CH3}
(In general formula (1), m represents an integer of 1 to 3, n represents an integer of 0 to 2, and multiple m and n may be the same or different.)

In the organic EL display device of the present embodiment, the pixel of the color filter is a cured product of the specific photosensitive coloring composition, so even when the color filter is formed on the organic EL layer, the effect of heat on the organic EL layer can be suppressed. Therefore, it is possible to obtain a high-quality organic EL display device having high brightness and high color reproducibility.
In addition, the organic EL display device of the present embodiment uses pixels whose color filters have the above-described specific spectral characteristics, so that the area defined by the color triangle connecting R (red), G (green), and B (blue) in the xy chromaticity diagram is expanded, and the display device has a wide color reproduction range (that is, high color reproducibility).
Hereinafter, regarding the organic EL display device of the present embodiment, the photosensitive coloring composition for pixel formation will be described first, and then the structure of the organic EL display device will be described.

1. Photosensitive coloring composition In the present embodiment, the photosensitive coloring composition contains at least a coloring agent (A), a photopolymerizable monomer (B), a photopolymerization initiator (C), and a resin (D), wherein the photopolymerizable monomer (B) contains at least a compound represented by general formula (1), and the photopolymerization initiator (C) contains at least an oxime ester photopolymerization initiator. As a result, an organic EL display device having high brightness and high color reproducibility and formed on a high-quality silicon substrate can be realized.

[Colorant (A)]
In the present embodiment, the coloring agent (A) adjusts the color tone of the pixels of the color filter so that specific spectral characteristics described later can be obtained, and can be appropriately selected and used from known pigments and dyes according to the color of a predetermined pixel.
Examples of the colorant for red pixels include a combination of one or more colorants selected from red and orange colorants and a yellow colorant used as necessary.
Examples of the colorant for green pixels include a combination of a green colorant and a colorant such as yellow that is used as necessary.
Further, the coloring agent for blue pixels includes one or more coloring agents selected from blue and purple. The coloring agent (A) for each pixel can be used singly or in combination of two or more.

As the pigment, both organic pigments and inorganic pigments can be suitably used. In addition, since the photosensitive coloring composition of the present embodiment is excellent in low-temperature curability, even dyes with low heat resistance compared to pigments can be suitably used.
In the present embodiment, the colorant (A) is preferably a pigment, more preferably an organic pigment, from the viewpoints of high color developability, excellent heat resistance, and particularly excellent thermal decomposition resistance.

<Pigment>
Specific examples of known organic pigments that can be used as colorants for the pixels of this embodiment are shown below by color index numbers.
As a red pigment, C.I. I. Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 37, 38, 41, 47, 48, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 50:1, 52:1, 52:2, 53, 53: 1,53:2,53:3,57,57:1,57:2,58:4,60,63,63:1,63:2,64,64:1,68,69,81,81:1,81:2,81:3,81:4,83,88,90:1,101,101:1,104,108,108:1,109,1 12, 113, 114, 122, 123, 144, 146, 147, 149, 151, 166, 168, 169, 170, 172, 173, 174, 175, 176, 177, 178, 179, 181, 184, 185, 187, 188, 190, 193, 194, 200, 202, 206, 207, 208, 209, 210, 214, 216, 220, 221, 224, 230, 231, 232, 233, 235, 236, 237, 238, 239, 242, 243, 245, 247, 249, 250, 251, 253, 254, 255, 256 , 257, 258, 259, 260, 262, 263, 264, 265, 266, 267, 268, 269, 270, 271, 272, 273, 274, 275, 276 and the like.
Examples of orange pigments include C.I. I. Pigment Orange 36, 38, 43, 51, 55, 59, 61 and the like.
Among these, C.I. I. Pigment Red 254, C.I. I. Pigment Red 177 is particularly preferred.

Examples of green pigments include C.I. I. Pigment Green 1, 2, 4, 7, 8, 10, 13, 14, 15, 17, 18, 19, 26, 36, 45, 48, 50, 51, 54, 55 or 58 can be mentioned. Among these, C.I. I. Pigment Green 7, 36 or 58, more preferably C.I. I. Pigment Pigment Green 36, C.I. I. Pigment Pigment Green 58.

Examples of yellow pigments include C.I. I. Pigment Yellow 1, 1:1, 2, 3, 4, 5, 6, 9, 10, 12, 13, 14, 16, 17, 24, 31, 32, 34, 35, 35:1, 36, 36: 1, 37, 37: 1, 40, 41, 42, 43, 48, 53, 55, 61, 62, 62: 1, 63, 65, 73, 74, 7 1, 128, 129, 133, 134, 136, 138, 139, 142, 147, 14 8, 150, 151, 153, 154, 155, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 172, 173, 174, 175, 176, 180, 181, 182, 183, 184, 185, 1 88, 189, 190, 191, 191:1, 192, 193, 194, 195, 196, 197, 198, 199, 200, 202, 203, 204, 205, 206, 207, 208 and the like. Among these, C.I. I. Pigment Yellow 83, 117, 129, 138, 139, 150, 154, 155, 180, or 185, more preferably C.I. I. Pigment Yellow 138, 139, 150, or 185, more preferably C.I. I. Pigment Yellow 139, C.I. I. Pigment Yellow 185.

Examples of blue pigments include C.I. I. Pigment Blue 1, 1:2, 9, 14, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 17, 19, 25, 27, 28, 29, 33, 35, 36, 56, 56:1, 60, 61, 61:1, 62, 63, 66, 67, 68, 71, 72, 73, 74, 75 , 76, 78, 79 and the like. Among these, C.I. I. Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, or 15:6, more preferably C.I. I. Pigment Blue 15:3, C.I. I. Pigment Blue 15:6.

Examples of purple pigments include C.I. I. Pigment Violet 1, 1:1, 2, 2:2, 3, 3:1, 3:3, 5, 5:1, 14, 15, 16, 19, 23, 25, 27, 29, 31, 32, 37, 39, 42, 44, 47, 49, 50 and the like. Among these, C.I. I. Pigment Violet 19 or 23, more preferably C.I. I. Pigment Violet 23.

Examples of inorganic pigments include barium sulfate, zinc white, lead sulfate, yellow lead, zinc yellow, red iron oxide (III), cadmium red, ultramarine blue, Prussian blue, chromium oxide green, cobalt green, amber, titanium black, synthetic iron black, titanium oxide, metal oxide powder such as iron tetroxide, metal sulfide powder, and metal powder. Inorganic pigments are used in combination with organic pigments in order to ensure good applicability, sensitivity, developability, etc. while balancing chroma and lightness.

(Refinement of pigment)
When using a pigment as a coloring agent, it is preferable to use it after making it fine. The method for refining the pigment is not particularly limited, and for example, any of wet grinding, dry grinding, and dissolution precipitation method can be used, and salt milling treatment by a kneader method, which is one type of wet grinding, can be performed.

The salt milling treatment is a treatment in which a mixture of a pigment, a water-soluble inorganic salt and a water-soluble organic solvent is mechanically kneaded while being heated using a kneader such as a kneader, a two-roll mill, a three-roll mill, a ball mill, an attritor, and a sand mill, followed by washing with water to remove the water-soluble inorganic salt and the water-soluble organic solvent. The water-soluble inorganic salt functions as a crushing aid, and the high hardness of the inorganic salt is used to crush the pigment during salt milling. By optimizing the conditions for the salt milling treatment of the pigment, it is possible to obtain a pigment having a very fine primary particle size, a narrow distribution width, and a sharp particle size distribution.

As the water-soluble inorganic salt, sodium chloride, barium chloride, potassium chloride, sodium sulfate, etc. can be used, but sodium chloride (salt) is preferably used from the viewpoint of cost. The water-soluble inorganic salt is preferably used in an amount of 50 to 2,000 parts by mass, most preferably 300 to 1,000 parts by mass, based on 100 parts by mass of the pigment, from the viewpoint of both processing efficiency and production efficiency.

The water-soluble organic solvent has the function of moistening the pigment and the water-soluble inorganic salt, and is not particularly limited as long as it dissolves (miscible in) water and does not substantially dissolve the inorganic salt used. However, since the temperature rises during salt milling and the solvent easily evaporates, a high boiling point solvent having a boiling point of 120° C. or higher is preferable from the viewpoint of safety. For example, 2-methoxyethanol, 2-butoxyethanol, 2-(isopentyloxy)ethanol, 2-(hexyloxy)ethanol, diethylene glycol, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol, triethylene glycol monomethyl ether, liquid polyethylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, liquid polypropylene glycol and the like are used. The water-soluble organic solvent is preferably used in an amount of 5 to 1,000 parts by mass, most preferably 50 to 500 parts by mass, per 100 parts by mass of the pigment.

When salt milling the pigment, a resin may be added as necessary. The type of resin used is not particularly limited, and natural resins, modified natural resins, synthetic resins, synthetic resins modified with natural resins, and the like can be used. The resins used are preferably solid at room temperature, water-insoluble, and more preferably partially soluble in the above organic solvents. The amount of the resin used is preferably in the range of 5 to 200 parts by mass with respect to 100 parts by mass of the pigment.

The primary particle size of the pigment is preferably 20 nm or more because it is well dispersed in the carrier. Moreover, it is preferably 100 nm or less because a color filter having a high contrast ratio can be formed. A particularly preferred range is from 25 to 85 nm. The primary particle size of the pigment is determined by a method of directly measuring the size of the primary particles from an electron micrograph of the pigment taken by a TEM (transmission electron microscope). Specifically, the short axis diameter and long axis diameter of the primary particles of each pigment are measured, and the average is used as the particle size of the pigment particles. Next, for 100 or more pigment particles, the volume of each particle is obtained by approximating it to the cube of the obtained particle size, and the volume average particle size is taken as the average primary particle size.
The coloring composition of the present embodiment contains an epoxy compound together with a specific pigment dispersant containing a thermally crosslinkable functional group, so that even when such a finely divided pigment is used, it has excellent resistance and can be a coloring composition for a color filter having a high brightness and contrast ratio.

<Dye>
A dye may be used as the colorant (A). Any of acid dyes, direct dyes, basic dyes, salt-forming dyes, oil-soluble dyes, disperse dyes, reactive dyes, mordant dyes, vat dyes, sulfur dyes, and the like can be used as dyes. Moreover, it may be in the form of a lake pigment obtained by converting a derivative of these or a dye into a lake.

In the case of acid dyes and direct dyes having an acidic group such as sulfonic acid or carboxylic acid, inorganic salts, quaternary ammonium salt compounds, tertiary amine compounds, secondary amine compounds, and nitrogen-containing compounds such as primary amine compounds can be salt-forming compounds.
Moreover, in the case of a basic dye, it can be used by forming a salt using an organic acid, perchloric acid, or a metal salt thereof.
Also, a dye having a polymerizable unsaturated group or an oxetane group in the dye skeleton may be used. Colored compositions using these dyes are excellent in heat resistance after curing.

Examples of dyes include azo dyes, methine dyes, azomethine dyes (indoaniline dyes, indophenol dyes, etc.), dipyrromethene dyes, quinone dyes (benzoquinone dyes, naphthoquinone dyes, anthraquinone dyes, anthrapyridone dyes, etc.), carbonium dyes (diphenylmethane dyes, triphenylmethane dyes, xanthene dyes, acridine dyes, etc.), quinoneimine dyes (oxazine dyes, etc.). dyes, thiazine dyes, etc.), azine dyes, polymethine dyes (oxonol dyes, merocyanine dyes, arylidene dyes, styryl dyes, cyanine dyes, squarylium dyes, croconium dyes, etc.), quinophthalone dyes, phthalocyanine dyes, subphthalocyanine dyes, perinone dyes, indigo dyes, thioindigo dyes, quinoline dyes, nitro dyes, nitroso dyes, diarylmethane dyes , triarylmethane dyes, perylene dyes, diketopyrrolopyrrole dyes, quinacridone dyes, anthanthrone dyes, isoindolinone dyes, isoindoline dyes, indanthrone dyes, coumarin dyes, pyranthrone dyes, flavanthrone dyes, cationic dyes, and metal complex dyes thereof.

Among these dye structures, azo dyes, xanthene dyes, cyanine dyes, triphenylmethane dyes, anthraquinone dyes, dipyrromethene dyes, squarylium dyes, quinophthalone dyes, phthalocyanine dyes, and subphthalocyanine dyes are preferred, and xanthene dyes, cyanine dyes, triphenylmethane dyes, anthraquinone dyes, dipyrromethene dyes, and phthalocyanine dyes are preferred from the viewpoint of color properties such as hue, color separation, and color unevenness. Nin-based dyes and xanthene-based dyes are more preferred, and xanthene-based dyes are even more preferred.

Xanthene-based dyes that can be preferably used exhibit red and purple colors, and may be in the form of oil-soluble dyes, acid dyes, direct dyes, or basic dyes, and may also be lake pigments.

Xanthene-based basic dyes are preferably used after being salted with an organic acid or perchloric acid. As the organic acid, it is preferable to use an organic sulfonic acid or an organic carboxylic acid. Among them, naphthalenesulfonic acid such as Bias acid and perchloric acid are preferably used from the standpoint of resistance.

Xanthene-based acid dyes can be used as salt-forming compounds by salt-forming using quaternary ammonium salt compounds, tertiary amine compounds, secondary amine compounds, primary amine compounds, etc., or resin components having these functional groups, or can be sulfonamidated and used as sulfonic acid amide compounds. A salt-forming compound of a xanthene-based acid dye and a sulfonic acid amide compound of a xanthene-based acid dye are preferable because they are excellent in hue and resistance. Further, it is more preferable to use a compound obtained by salting a xanthene-based acid dye with a quaternary ammonium salt and a sulfonamide compound obtained by sulfonamidating a xanthene-based acid dye.

Among xanthene dyes, rhodamine dyes are preferable because they are excellent in color developability and durability.

Examples of xanthene-based oil-soluble dyes include C.I. I. Solvent Red 35, C.I. I. Solvent Red 36, C.I. I. Solvent Red 42, C.I. I. Solvent Red 43, C.I. I. Solvent Red 44, C.I. I. Solvent Red 45, C.I. I. Solvent Red 46, C.I. I. Solvent Red 47, C.I. I. Solvent Red 48, C.I. I. Solvent Red 49, C.I. I. Solvent Red 72, C.I. I. Solven Red 73, C.I. I. Solvent Red 109, C.I. I. Solvent Red 140, C.I. I. Solvent Red 141, C.I. I. Solvent Red 237, C.I. I. Solvent Red 246, C.I. I. solvent violet 2, C.I. I. and Solvent Violet 10.
Among them, C.I. I. Solvent Red 35, C.I. I. Solvent Red 36, C.I. I. Solvent Red 49, C.I. I. Solvent Red 109, C.I. I. Solvent Red 237, C.I. I. Solvent Red 246, C.I. I. Solvent Violet 2 is more preferred.

Examples of xanthene-based basic dyes include C.I. I. Basic Red 1 (Rhodamine 6GCP), 8 (Rhodamine G), C.I. I. Basic Violet 10 (Rhodamine B) and the like. Among them, C.I. I. Basic Red 1, C.I. I. Basic Violet 10 is preferably used.

Examples of xanthene-based acid dyes include C.I. I. Acid Red 51 (erythrosine (food red No. 3)), C.I. I. Acid Red 52 (acid rhodamine), C.I. I. Acid Red 87 (Eosin G (Edible Red No. 103)), C.I. I. Acid Red 92 (Acid Phloxine PB (Edible Red No. 104)), C.I. I. Acid Red 289, C.I. I. Acid Red 388, Rose Bengal B (Edible Red No. 5), Acid Rhodamine G, C.I. I. It is preferred to use Acid Violet 9.
Among them, C.I. I. Acid Red 87, C.I. I. Acid Red 92, C.I. I. Acid Red 388, or C.I., which is a rhodamine acid dye. I. Acid Red 52 (acid rhodamine), C.I. I. Acid Red 289, Acid Rhodamine G, C.I. I. More preferably, Acid Violet 9 is used.
Among these, C.I. I. Acid Red 52, C.I. I. Most preferably, Acid Red 289 is used.

The acid dye (not limited to xanthene) is preferably a salt-forming compound of an acid dye and a nitrogen-containing compound, such as a quaternary ammonium salt compound, a tertiary amine compound, a secondary amine compound, a primary amine compound, or the like, or by salting using a resin component having these functional groups to form an acid dye salt-forming compound, which is preferable because high heat resistance, light resistance, and solvent resistance can be imparted. Acid dyes can be imparted with high heat resistance, light resistance and solvent resistance by sulfonamidation.
Further, it may be a salt-forming compound of an acid dye and a compound having an onium base. Among them, the compound having an onium base is a resin having a cationic group in a side chain, so that the coloring composition can have excellent brightness and resistance.

Primary amine compounds include aliphatics such as methylamine, ethylamine, propylamine, isopropylamine, butylamine, amylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, undecylamine, dodecylamine (laurylamine), tridodecylamine, tetradecylamine (myristylamine), pentadecylamine, cetylamine, stearylamine, oleylamine, cocoalkylamine, tallow alkylamine, hardened tallow alkylamine, and allylamine. Unsaturated primary amines, aniline, benzylamine and the like can be mentioned.

Secondary amine compounds include aliphatic unsaturated secondary amines such as dimethylamine, diethylamine, dipropylamine, diisopropylamine, dibutylamine, diamylamine and diallylamine;

Tertiary amine compounds include trimethylamine, triethylamine, tripropylamine, tributylamine, triamylamine, dimethylaniline, diethylaniline, tribenzylamine and the like.

(Quaternary ammonium salt compound)
When the organic dye is an acid dye, it is preferably used as a salt-forming compound (a) comprising an acid dye and a quaternary ammonium salt compound. The quaternary ammonium salt compound as the counter component of the acid dye is described below. The quaternary ammonium salt compound (a) functions as a counter for acid dyes by having an amino group.

A preferred form of the quaternary ammonium salt compound, which is the counter component of the salt-forming compound, is colorless or white. Here, colorless or white means a so-called transparent state, and is defined as a state in which the transmittance is 95% or more, preferably 98% or more in the entire wavelength range of 400 to 700 nm in the visible light region. That is, it is preferable that it does not interfere with the color development of the dye component and does not cause color change.

The molecular weight of the counter portion, which is the cationic component of the quaternary ammonium salt compound, is preferably in the range of 190-900. If the molecular weight is less than 190, the light resistance and heat resistance may be lowered, and the solubility in solvents may be lowered. On the other hand, if the molecular weight exceeds 900, the ratio of the coloring component in the molecule will decrease, resulting in a decrease in color developability and brightness. More preferably, the molecular weight of the counter moiety is in the range of 240-850. Particularly preferred are counter moieties with molecular weights in the range of 350-800. Here, the molecular weight was calculated based on the structural formula, and the atomic weight of C was 12, the atomic weight of H was 1, and the atomic weight of N was 14.

As the quaternary ammonium salt compound, a compound represented by the following general formula (4) is preferable.

（一般式（４）中、Ｒ^３１～Ｒ^３４は、それぞれ独立に、炭素数１～２０のアルキル基又はベンジル基を示し、Ｒ^３１～Ｒ^３４の少なくとも２つ以上が、炭素数が５～２０個である。Ｘ^１－は無機又は有機のアニオンを表す。）

(In general formula (4), R ³¹ to R ³⁴ each independently represent an alkyl group having 1 to 20 carbon atoms or a benzyl group, and at least two or more of R ³¹ to R ³⁴ have 5 to 20 carbon atoms. X ^1- represents an inorganic or organic anion.)

When at least two or more of R ³¹ to R ³⁴ have 5 to 20 carbon atoms, good solubility in a solvent is obtained. If there are three or more alkyl groups having a carbon number of less than 5, the solubility in a solvent is deteriorated, and foreign matter is likely to occur in the coating film. In addition, if an alkyl group having more than 20 carbon atoms is present, the salt-forming compound (a) will be impaired in color development.

X ^1- may be an inorganic or organic anion, preferably a halogen, and preferably a chloride ion (anion).

The quaternary ammonium salt compounds include tetramethylammonium chloride, tetraethylammonium chloride, monostearyltrimethylammonium chloride, distearyldimethylammonium chloride, tristearylmonomethylammonium chloride, cetyltrimethylammonium chloride, trioctylmethylammonium chloride, dioctyldimethylammonium chloride, monolauryltrimethylammonium chloride, dilauryldimethylammonium chloride, trilaurylmethylammonium chloride, triamylbenzylammonium chloride, trihexylbenzylammonium chloride, and trioctylbenzylammonium chloride. chloride, trilaurylbenzylammonium chloride, benzyldimethylstearylammonium chloride, benzyldimethyloctylammonium chloride, dialkyl (alkyl is C14-C18) dimethylammonium chloride (hardened beef tallow), and the like.

Specific products of quaternary ammonium salt compounds include, for example, Kotamine 24P, Kotamine 86P Conc, Kotamine 60W, Kotamine 86W, Kotamine D86P, Sanizol C, Sanizol B-50 manufactured by Kao Corporation, and Arcade 210-80E, 2C-75, 2HT-75, 2HT flakes, 2O-75I, 2HP-75 and 2HP flakes manufactured by Lion Corporation. Among them, Cortamine D86P (distearyldimethylammonium chloride) and Arkard 2HT-75 (dialkyl (alkyl is C14-C18) dimethylammonium chloride) can be mentioned.

(Resin having a cationic group in the side chain)
When the organic dye used in this embodiment is an acid dye, it is also preferably used as a salt-forming compound (a') comprising an acid dye and a resin having a cationic group in its side chain. The resin having a cationic group in the side chain for obtaining the salt-forming compound (a') used in this embodiment will be described.
The resin having a cationic group in the side chain for obtaining the salt-forming compound is not particularly limited as long as it has at least one onium base in the side chain. Preferred onium salt structures, from the viewpoint of availability, are preferably ammonium salts, iodonium salts, sulfonium salts, diazonium salts, and phosphonium salts, and more preferably ammonium salts, iodonium salts, and sulfonium salts in consideration of storage stability (thermal stability). Ammonium salts are more preferred.

When preparing a photosensitive coloring composition containing a salt-forming compound (a ') and expressing properties as a color filter, it is preferable to use the same resin as the binder resin constituting the photosensitive coloring composition. When an acrylic resin is used as the binder resin of the photosensitive coloring composition, the resin having a cationic group in the side chain for obtaining the salt-forming compound (a') is preferably an acrylic resin.

As the resin having a cationic group in its side chain, an alkali resin containing a structural unit represented by the following general formula (5) is preferred. A salt-forming compound can be obtained by forming a salt between the cationic group in the general formula (5) and the anionic group of the xanthene-based acid dye.

（一般式（５）中、Ｒ^４１は水素原子、又は置換もしくは無置換のアルキル基を表す。Ｒ^４２～Ｒ^４４は、それぞれ独立に、水素原子、置換されていてもよいアルキル基、置換されていてもよいアルケニル基、又は置換されていてもよいアリール基を表し、Ｒ^４２～Ｒ^４４のうち２つが互いに結合して環を形成しても良い。Ｑはアルキレン基、アリーレン基、－ＣＯＮＨ－Ｒ^４５－、－ＣＯＯ－Ｒ^４５－を表し、Ｒ^４５はアルキレン基を表す。Ｘ^２－は無機又は有機のアニオンを表す。）

(In general formula (5), R ⁴¹ represents a hydrogen atom or a substituted or unsubstituted alkyl group. R ⁴² to R ⁴⁴ each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, or an optionally substituted aryl group, and two of R ⁴² to R ⁴⁴ may be bonded to each other to form a ring. Q is an alkylene group, an arylene group, —CONH—R ⁴⁵ —, —COO—R ⁴⁵ -, R ⁴⁵ represents an alkylene group, and X ^2- represents an inorganic or organic anion.)

Examples of the alkyl group for R ⁴¹ include methyl group, ethyl group, propyl group, n-butyl group, i-butyl group, t-butyl group, n-hexyl group and cyclohexyl group. As the alkyl group, an alkyl group having 1 to 12 carbon atoms is preferable, an alkyl group having 1 to 8 carbon atoms is more preferable, and an alkyl group having 1 to 4 carbon atoms is particularly preferable.

When the alkyl group represented by R ⁴¹ has a substituent, examples of the substituent include a hydroxyl group and an alkoxyl group.

Among the above, R ⁴¹ is most preferably a hydrogen atom or a methyl group.

Ｒ ^４２ ～Ｒ ^４４におけるアルキル基としては、例えば、直鎖アルキル基（メチル、エチル、ｎ－プロピル、ｎ－ブチル、ｎ－ペンチル、ｎ－オクチル、ｎ－デシル、ｎ－ドデシル、ｎ－テトラデシル、ｎ－ヘキサデシル及びｎ－オクタデシル等）、分岐アルキル基（イソプロピル、イソブチル、ｓｅｃ－ブチル、ｔｅｒｔ－ブチル、イソペンチル、ネオペンチル、ｔｅｒｔ－ペンチル、イソヘキシル、２－エチルヘキシル及び１，１，３，３－テトラメチルブチル等）、シクロアルキル基（シクロプロピル、シクロブチル、シクロペンチル及びシクロヘキシル等）及び架橋環式アルキル基（ノルボルニル、アダマンチル及びピナニル等）が挙げられる。 The alkyl group is preferably an alkyl group having 1 to 18 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms.

Examples of alkenyl groups for R ⁴² to R ⁴⁴ include linear or branched alkenyl groups (vinyl, allyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-1-propenyl and 2-methyl-2-propenyl, etc.), cycloalkenyl groups (2-cyclohexenyl and 3-propenyl). -cyclohexenyl, etc.). The alkenyl group is preferably an alkenyl group having 2 to 18 carbon atoms, more preferably an alkenyl group having 2 to 8 carbon atoms.

Examples of aryl groups for R ⁴² to R ⁴⁴ include monocyclic aryl groups (phenyl etc.), condensed polycyclic aryl groups (naphthyl, anthracenyl, phenanthrenyl, anthraquinolyl, fluorenyl, naphthoquinolyl etc.) and aromatic heterocyclic hydrocarbon groups (thienyl (group derived from thiophene), furyl (group derived from furan), pyranyl (group derived from pyran) and pyridyl (group derived from pyridine). , 9-oxoxanthenyl (group derived from xanthone) and 9-oxothioxanthenyl (group derived from thioxanthone), etc.).

When the alkyl group, alkenyl group, or aryl group represented by R ⁴² to R ⁴⁴ has a substituent, the substituent includes, for example, a halogen atom, a hydroxyl group, an alkoxyl group, an aryloxy group, an alkenyl group, an acyl group, an alkoxycarbonyl group, a carboxyl group, a phenyl group, and the like. Among these substituents, halogen atoms, hydroxyl groups, alkoxyl groups, and phenyl groups are particularly preferred.

From the viewpoint of stability, R ⁴² to R ⁴⁴ are preferably optionally substituted alkyl groups, more preferably unsubstituted alkyl groups.

Also, two of R ⁴² to R ⁴⁴ may combine with each other to form a ring.

In general formula (5), the component Q that connects the vinyl moiety and the ammonium base represents ^an alkylene group, an arylene group, ^-CONH -R ⁴⁵ -, and -COO-R ⁴⁵ -, and R ⁴⁵ represents an alkylene group. Further, ^R45 is more preferably a methylene group, an ethylene group, a propylene group or a butylene group, and particularly preferably an ethylene group.

The component X ^2- in general formula (5), which constitutes the counter anion of the resin, may be an inorganic or organic anion. As the counter anion, known ones can be employed without limitation, and specific examples include hydroxide ion; halogen ion such as chloride ion, bromide ion and iodide ion; carboxylate ion such as formate ion and acetate ion; Halogen ions and carboxylate ions are preferred, and halogen ions are most preferred, from the viewpoints of suitability for synthesis and stability. When the counter anion is an organic acid ion such as carboxylate ion, the organic acid ion may be covalently bonded to the resin to form an inner salt.

One method of introducing an oxetane group into a resin having a cationic group in its side chain is to copolymerize an ethylenically unsaturated monomer containing an oxetane structure with an ethylenically unsaturated monomer corresponding to the cationic group represented by general formula (5). Examples of ethylenically unsaturated monomers having an oxetane group include (3-methyl-3-oxetanyl)methyl (meth)acrylate, (3-ethyl-3-oxetanyl)methyl (meth)acrylate, (3-butyl-3-oxetanyl)methyl (meth)acrylate, (3-hexyltyl-3-oxetanyl)methyl (meth)acrylate and the like. Examples of commercially available products include ETERNACOLL OXMA (manufactured by Ube Industries, Ltd.), OXE-10, and OXE-30 (manufactured by Osaka Organic Chemical Industry Co., Ltd.).

(salt formation)
A salt-forming compound of an acid dye and a nitrogen-containing compound or a resin having a cationic group in a side chain can be produced by a conventionally known method. A specific technique is disclosed in Japanese Patent Application Laid-Open No. 11-72969. As an example using a xanthene-based acid dye, after dissolving the xanthene-based acid dye in water, a quaternary ammonium salt compound may be added, and the solution may be subjected to chlorination while stirring. Here, a salt-forming compound is obtained in which the sulfonic acid group (--SO ₃ H) and sodium sulfonate group (--SO ₃ Na) in the xanthene acid dye are combined with the ammonium group (NH4 ⁺ ) in the quaternary ammonium salt compound. In place of water, methanol and ethanol are also usable solvents for chlorination.

Further, the salt-forming compound can be easily obtained by stirring or vibrating an aqueous solution in which a resin having a cationic group in a side chain represented by the general formula (4) and an acid dye are dissolved, or by mixing an aqueous solution of a resin having a cationic group in a side chain represented by the general formula (4) and an aqueous solution of an acid dye under stirring or vibrating. In an aqueous solution, the ammonium group of the resin and the anionic group of the acid dye are ionized, and they form an ionic bond, and the ion-bonded portion becomes water-insoluble and precipitates. On the contrary, since the salt composed of the counter anion of the resin and the counter cation of the acid dye is water-soluble, it can be removed by washing with water or the like. The resin having a cationic group in the side chain and the acid dye to be used may be of a single type, or may be of a plurality of types having different structures.
Also, with other acid dyes, a salt-forming compound with a nitrogen-containing compound or a resin having a cationic group in the side chain can be obtained in the same manner as for xanthene dyes.

(sulfonic acid amide compound)
The acid dye may be a sulfonic acid amide compound obtained by reacting a sulfonic acid amide compound with an anionic dye.
A sulfonic acid amide compound of an acid dye that can be preferably used for an acid dye can be produced by chlorinating an acid dye having —SO ₃ H or —SO ₃ Na by a conventional method to convert —SO ₃ H to —SO ₂ Cl, and reacting this compound with an amine having a —NH ₂ group.
As amine compounds that can be preferably used in sulfonamidation, specifically, 2-ethylhexylamine, dodecylamine, 3-decyloxypropylamine, 3-(2-ethylhexyloxy)propylamine, 3-ethoxypropylamine, cyclohexylamine and the like are preferably used.

As an example of xanthene-based acid dyes, C.I. I. When obtaining a sulfonic acid amide compound obtained by modifying Acid Red 289 with 3-(2-ethylhexyloxy)propylamine, C.I. I. Acid Red 289 is sulfonyl chlorided and then reacted with the theoretical equivalent of 3-(2-ethylhexyloxy)propylamine in dioxane to give C.I. I. A sulfonic acid amide compound of Acid Red 289 may be obtained.
Also, C.I. I. In the case of obtaining a sulfonic acid amide compound by modifying Acid Red 52 with 3-(2-ethylhexyloxy)propylamine, C.I. I. Acid Red 52 is sulfonyl chlorided and then reacted with the theoretical equivalent of 3-(2-ethylhexyloxy)propylamine in dioxane to give C.I. I. A sulfonic acid amide compound of Acid Red 52 may be obtained.
Also, with other acid dyes, sulfonic acid amide compounds can be obtained in the same manner as with xanthene dyes.

In this embodiment, the content of the coloring agent (A) in the photosensitive coloring composition is appropriately adjusted for each pixel from the viewpoint of achieving desired optical properties and obtaining sufficient color reproducibility.
In the case of the photosensitive coloring composition for red pixels, the content of the coloring agent (A) is preferably 10% by mass or more and 90% by mass or less, more preferably 20% by mass or more and 80% by mass or less, and still more preferably 24% by mass or more and 67% by mass or less, relative to the total solid content of the photosensitive coloring composition.
In the case of a photosensitive coloring composition for green pixels, the content of the coloring agent (A) is preferably 10% by mass or more and 80% by mass or less, more preferably 20% by mass or more and 70% by mass or less, and still more preferably 30% by mass or more and 55% by mass or less, relative to the total solid content of the photosensitive coloring composition.
In the case of the photosensitive coloring composition for blue pixels, the content of the coloring agent (A) is preferably 10% by mass or more and 80% by mass or less, more preferably 20% by mass or more and 70% by mass or less, and still more preferably 30% by mass or more and 47% by mass or less, relative to the total solid content of the photosensitive coloring composition.
If it is at least the above lower limit, desired optical characteristics can be achieved and sufficient color reproducibility can be obtained. On the other hand, when it is equal to or less than the above upper limit value, the stability of the photosensitive coloring composition is excellent.
In this embodiment, the solid content refers to all components other than the solvent constituting the photosensitive coloring composition, that is, components remaining after curing the photosensitive coloring composition.

The maximum transmittance of light in the wavelength range of 450 nm to 560 nm is 0.4% or less, and the transmittance of light in the wavelength range of 600 nm to 700 nm is 80% or more and less than 100%. The combination of colorants for forming a red pixel that satisfies is not particularly limited, but a combination of a red pigment and a yellow pigment is preferable from the viewpoint of easy preparation that satisfies the spectral characteristics and excellent weather resistance.
When a red pigment and a yellow pigment are combined, the mixing ratio of the yellow pigment is preferably 1 to 60 parts by mass, more preferably 2 to 50 parts by mass, and still more preferably 5 to 30 parts by mass with respect to 100 parts by mass of the red pigment.

The maximum spectral transmittance of light in the wavelength range of 400 nm to 470 nm is 2% or less, the transmittance of light at a wavelength of 520 nm is 70% or more, and the transmittance of light at a wavelength of 550 nm is 60% or less. The combination of colorants for forming a green pixel is not particularly limited, but a combination of a green pigment and a blue pigment is preferable, and a combination of a yellow pigment is more preferable because preparation that satisfies the spectral characteristics is easy and weather resistance is excellent.
When a green pigment and a blue pigment are combined, the content of the blue pigment is preferably 1 to 60 parts by mass, more preferably 2 to 50 parts by mass, and even more preferably 5 to 45 parts by mass with respect to 100 parts by mass of the green pigment. Further, when a yellow pigment is combined, the mixing ratio of the yellow pigment is preferably 10 to 90 parts by mass, more preferably 30 to 85 parts by mass, and even more preferably 50 to 75 parts by mass with respect to 100 parts by mass of the green pigment.

The combination of colorants for forming a blue pixel that satisfies the spectral transmittance of less than 20% maximum light transmittance in the wavelength range of 500 nm to 560 nm is not particularly limited, but a combination of a blue pigment and a violet pigment is preferable from the viewpoint of ease of preparation that satisfies the spectral characteristics and excellent weather resistance.
When a blue pigment and a purple pigment are combined, the blending ratio of the purple pigment is preferably 20 to 120 parts by mass, more preferably 60 to 80 parts by mass, and even more preferably 50 to 70 parts by mass with respect to 100 parts by mass of the blue pigment.

[Photopolymerizable monomer (B)]
In this embodiment, the photopolymerizable monomer (B) contains at least a compound represented by the following general formula (1), and may further contain other photopolymerizable monomers as necessary.
By using the compound represented by the general formula (1), both adhesion to the substrate and resolution of the resist pattern can be achieved.

General formula (1)
[ _CH2 =CHC(=O)-( _OCmH2m ) _{n -OCH2 ] 3 - CCH2CH3}
(In general formula (1), m represents an integer of 1 to 3, n represents an integer of 0 to 2, and multiple m and n may be the same or different.)

Specific examples of the compound represented by formula (1) include trimethylolpropane triacrylate, trimethylolpropane EO-modified triacrylate, and trimethylolpropane PO-modified triacrylate.
The compounds represented by formula (1) can be used singly or in combination of two or more.

<Other photopolymerizable monomers>
Moreover, the photopolymerizable compound (B) in this embodiment may contain other photopolymerizable monomers. Other photopolymerizable monomers include known (meth)acrylate monomers. Specifically, for example, methyl (meth)acrylate, ethyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, cyclohexyl (meth)acrylate, β-carboxyethyl (meth)acrylate, polyethylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, triethylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, 1,6-hexanediol) Various acrylic and methacrylic acid esters such as diglycidyl ether di(meth)acrylate, bisphenol A diglycidyl ether di(meth)acrylate, neopentyl glycol diglycidyl ether di(meth)acrylate, dipentaerythritol hexa(meth)acrylate, dipentaerythritol penta(meth)acrylate, tricyclodecanyl (meth)acrylate, ester acrylate, methylolated melamine (meth)acrylate, epoxy (meth)acrylate, (meth)acrylic acid, styrene, vinyl acetate, hydroxyethyl vinyl ether , ethylene glycol divinyl ether, pentaerythritol trivinyl ether, (meth)acrylamide, N-hydroxymethyl(meth)acrylamide, N-vinylformamide, acrylonitrile and the like, but are not limited thereto.
A photopolymerizable compound can be used individually by 1 type or in mixture of 2 or more types.

The content of the photopolymerizable monomer (B) with respect to the total solid content in the photosensitive coloring composition is preferably 5 to 40% by mass. By setting the thickness within the above range, it is possible to prevent peeling when forming a fine pattern, and to suppress the tapered portion of the pattern from being elongated, thereby forming a high-definition fine pixel pattern. Furthermore, the content of the compound represented by the general formula (1) contained in the photopolymerizable monomer (B) is preferably 50 to 100% by mass, more preferably 60% by mass or more, relative to the total amount of the photopolymerizable monomer (B). By setting the amount within the above range, excellent adhesion of the coating film to the substrate during development and chemical resistance can be obtained.

[Photoinitiator (C)]
The photopolymerization initiator (C) in this embodiment contains an oxime ester photopolymerization initiator, and may further contain other photopolymerization initiators as necessary. The photosensitive coloring composition containing the oxime ester-based photopolymerization initiator can be a photosensitive coloring composition that has ultraviolet irradiation curability and solvent developability or alkali developability. Therefore, according to the said photosensitive coloring composition, a pixel can be formed by the photolithography method. In addition, by using the oxime ester-based relative polymerization initiator, a photosensitive coloring composition having excellent color characteristics and chemical resistance and good patterning properties can be obtained.

<Oxime ester photopolymerization initiator>
In the oxime ester photopolymerization initiator, upon absorption of ultraviolet rays, the N—O bond of the oxime is cleaved to generate iminyl radicals and alkyloxy radicals. Since these radicals are further decomposed to generate highly active radicals, a pattern can be formed with a small amount of exposure. When the coloring agent concentration of the photosensitive coloring composition is high, the UV transmittance of the coating film may be low, and the curing degree of the coating film may be low. Since the photosensitive coloring composition of the present embodiment contains an oxime ester photopolymerization initiator with high quantum efficiency, it has excellent curability even when the concentration of the coloring agent is high.
As the oxime ester photopolymerization initiator, among them, an oxime ester photopolymerization initiator represented by the following general formula (2) or (3) is preferable, and an oxime ester photopolymerization initiator represented by general formula (2) is more preferable.

(Oxime ester photopolymerization initiator represented by general formula (2))

（一般式（２）中、Ｚは直接結合、又は－Ｃ（＝Ｏ）－基を表し、Ｒ^１は置換基を有してもよい炭素数１～２０のアルキル基を表し、Ｒ^２は置換基を有してもよい炭素数１～２０のアルキル基、又は置換基を有してもよいアリール基を表し、Ｒ^３～Ｒ^１０はそれぞれ独立して、水素原子、置換基を有してもよい炭素数１～２０のアルキル基、置換基を有してもよいアリール基、ニトロ基、又はＲ^１１－Ｃ（＝Ｏ）－基を表す。Ｒ^１１は置換基を有してもよいアリール基を表す。）

(In general formula (2), Z represents a direct bond or a -C(=O)- group, R ¹ represents an optionally substituted C 1-20 alkyl group, R ² represents an optionally substituted C 1-20 alkyl group or an optionally substituted aryl group, and R ³ to R ¹⁰ each independently represents a hydrogen atom, an optionally substituted C 1-20 alkyl group, an optionally substituted aryl group, or a nitro group. , or represents an R ¹¹ -C(=O)- group.R ¹¹ represents an aryl group which may have a substituent.)

Examples of alkyl groups having 1 to 20 carbon atoms in R ¹ to R ¹⁰ include linear alkyl groups such as methyl group, ethyl group, propyl group, butyl group, hexyl group, octyl group and dodecyl group.
Examples of the aryl group for R ² to R ¹¹ include phenyl group, naphthyl group, anthracenyl group and the like.
The fact that Z is a direct bond means that Z does not have an atom and two atoms that are connected to Z in general formula (2) are directly bonded.

The substituent that the alkyl group and the aryl group may have means that the alkyl group or the aryl group may have a substituent instead of a hydrogen atom. Examples of such substituents include halogen atoms such as fluorine, chlorine, bromine and iodine atoms; alkoxy groups such as methoxy, ethoxy and tert-butoxy; aryloxy groups such as phenoxy and p-tolyloxy; alkoxycarbonyl groups such as methoxycarbonyl, butoxycarbonyl and phenoxycarbonyl; acyl groups such as acryloyl group, methacryloyl group and methoxalyl group; alkylsulfanyl groups such as methylsulfanyl group and tert-butylsulfanyl group; arylsulfanyl groups such as phenylsulfanyl group and p-tolylsulfanyl group; alkylamino groups such as methylamino group and cyclohexylamino group; amino group; methyl group, ethyl group, tert-butyl group, dodecyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclooctadecyl group; Myl group, mercapto group, sulfo group, mesyl group, p-toluenesulfonyl group, amino group, nitro group, cyano group, trifluoromethyl group, trichloromethyl group, trimethylsilyl group, phosphinico group, phosphono group, trimethylammoniumyl group, dimethylsulfoniumyl group, triphenylphenacylphosphoniumyl group and the like.
One or more or more than one of these substituents may be present, and the hydrogen atoms of these substituents may be further substituted with other substituents.

In the oxime ester photopolymerization initiator represented by the general formula (2), Z is a direct bond or a -C(=O)- group, R ¹ is an optionally substituted C 1-20 alkyl group, R ² is an optionally substituted C 1-20 alkyl group or an optionally substituted aryl group, and R ³ to R ¹⁰ are each independently a hydrogen atom or an optionally substituted C 1-20 photopolymerization initiator. It is preferably an alkyl group, an optionally substituted aryl group, a nitro group, or an R ¹¹ -CO- group. Among them, it is more preferable that R ⁴ to R ⁶ and R ⁸ to R ¹⁰ are hydrogen atoms, R ⁷ is a hydrogen atom or R ¹¹ —CO— group, and R ¹¹ is an aryl group which may have a substituent.

As the oxime ester photopolymerization initiator represented by the general formula (2), compounds represented by the following chemical formula (2-1) or (2-2) are preferred.

(Oxime ester photopolymerization initiator represented by general formula (3))

（一般式（３）中、Ｒ^２１及びＲ^２２は、それぞれ独立して、水素原子、置換基を有してもよい炭素数１～２０のアルキル基、又は置換基を有してもよいアリール基であり、Ｒ^２３及びＲ^２４は、それぞれ独立して、水素原子、置換基を有してもよい炭素数１～２０のアルキル基、又は置換基を有してもよいアリール基であり、Ｒ^２５は、水素原子、置換基を有してもよい炭素数１～２０のアルキル基、置換基を有してもよいアリール基、又はＲ^２６－ＣＯ－基であり、Ｒ^２６は、置換基を有してもよい炭素数１～２０のアルキル基、置換基を有してもよいアリール基、又は複素環基である。）

(In general formula (3), R²¹and R²²are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted aryl group;²³and R²⁴are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted aryl group;²⁵is a hydrogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, an optionally substituted aryl group, or R²⁶-CO- group, and R²⁶is an optionally substituted alkyl group having 1 to 20 carbon atoms, an optionally substituted aryl group, or a heterocyclic group. )

The alkyl group having 1 to 20 carbon atoms for R ²¹ to R ²⁶ can be the same as the alkyl group having 1 to 20 carbon atoms for R ¹ to R ¹⁰ .
The aryl group for R ²¹ to R ²⁶ can be the same as the aryl group for R ² to R ¹¹ above.
Examples of the heterocyclic ring in the heterocyclic group of R ²⁶ include furan, thiophene, pyrrole, oxazole, thiazole, imidazole, pyrazole, pyran, pyrone, pyridine, pyrone, pyridazine, pyrimidine, pyrazine, benzofuran, thionaphthene, indole, carbazole, coumarin, quinoline, phthalazine, quinoxaline and the like.
Further, the substituents that the alkyl group and the aryl group may have may be the same as the substituents in the general formula (2).

In the oxime ester photopolymerization initiator represented by the general formula (3), it is preferable that R ²¹ is an aryl group which may have a substituent, R ²² is an alkyl group having 1 to 20 carbon atoms which may have a substituent, R ²³ and R ²⁴ are hydrogen atoms, and R ²⁵ is a hydrogen atom or an R ²⁶ —CO— group.

As the oxime ester photopolymerization initiator represented by the general formula (3), a compound represented by the following chemical formula (3-1) is preferable.

(Other photopolymerization initiators)
In addition, the photopolymerization initiator (C) in this implementation may further contain other photopolymerization initiators. Other photopolymerizable initiators include, for example, 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexylphenyl ketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl ) methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone, acetophenone compounds such as 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one; benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzyl dimethyl ketal; benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone-based compounds such as benzophenone, 4-benzoyl-4'-methyldiphenylsulfide, 3,3',4,4'-tetra(t-butylperoxycarbonyl)benzophenone; thioxanthone-based compounds such as thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone, and 2,4-diethylthioxanthone; 2,4,6-trichloro-s-triazine, 2-phenyl-4,6 -bis(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine, 2-piperonyl-4,6-bis(trichloromethyl)-s-triazine, 2,4-bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphth-1-yl)-4,6 -Bis(trichloromethyl)-s-triazine, 2-(4-methoxy-naphth-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2,4-trichloromethyl-(piperonyl)-6-triazine, 2,4-trichloromethyl-(4'-methoxystyryl)-6-triazine and other triazine compounds; bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, 2,4,6-trimethylbenzoyl phosphine compounds such as diphenylphosphine oxide; quinone compounds such as 9,10-phenanthrenequinone, camphorquinone and ethylanthraquinone; borate compounds; carbazole compounds; imidazole compounds;
These photopolymerization initiators can be used singly or as a mixture of two or more at an arbitrary ratio as required.
Commercially available photopolymerization initiators include acetophenone-based compounds, all of which are manufactured by BASF and include "IRGACURE 907" (2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one), "IRGACURE 369" (2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone), "IRGACURE 379" 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, phosphine-based compounds are all manufactured by BASF and include "IRGACURE 819" (bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide), "IRGACURE TPO" (2,4,6-trimethylbenzoyldiphenylphosphine oxide) and the like.

The content of the photopolymerization initiator (C) is preferably 2 to 50 parts by mass with respect to 100 parts by mass of the colorant (A), and more preferably 2 to 30 parts by mass from the viewpoint of photocurability and developability. When the photopolymerization initiator (C) is 2 parts by mass or more, the adhesiveness to the substrate is excellent. Moreover, when the photopolymerization initiator (C) is 50 parts by mass or less, the resolution is excellent.

[Sensitizer]
The photosensitive coloring composition of this embodiment may further contain a sensitizer.
Sensitizers include unsaturated ketones such as chalcone derivatives and dibenzalacetone; 1,2-diketone derivatives such as benzyl and camphorquinone; polymethine dyes such as benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, anthraquinone derivatives, xanthene derivatives, thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, and oxonol derivatives; , thiazine derivatives, oxazine derivatives, indoline derivatives, azulene derivatives, azulenium derivatives, squarylium derivatives, porphyrin derivatives, tetraphenylporphyrin derivatives, triarylmethane derivatives, tetrabenzoporphyrin derivatives, tetrapyrazinoporphyrazine derivatives, phthalocyanine derivatives, tetraazaporphyrazine derivatives, tetraquinoxalyloporphyrazine derivatives, naphthalocyanine derivatives, subphthalocyanine derivatives, pyrylium derivatives, thiopyrylium derivatives, tetraphyrin derivatives, annulene derivatives, spiro pyran derivatives, spirooxazine derivatives, thiospiropyran derivatives, metal arene complexes, organic ruthenium complexes, or Michler's ketone derivatives, α-acyloxyesters, acylphosphine oxides, methylphenylglyoxylate, benzyl, 9,10-phenanthrenequinone, camphorquinone, ethylanthraquinone, 4,4'-diethylisophthalophenone, 3,3' or 4,4'-tetra(t-butylperoxycarbonyl)benzophenone, 4,4'- bis(diethylamino)benzophenone and the like.

Among the above sensitizers, thioxanthone derivatives, Michler's ketone derivatives, and carbazole derivatives can be mentioned as sensitizers capable of particularly suitable sensitization. More specifically, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 2,4-dichlorothioxanthone, 2-isopropylthioxanthone, 4-isopropylthioxanthone, 1-chloro-4-propoxythioxanthone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(ethylmethylamino)benzophenone, N-ethylcarbazole, 3-benzoyl-N-ethylcarbazole sol, 3,6-dibenzoyl-N-ethylcarbazole and the like.

In addition, commercially available sensitizers include "KAYACURE DETX-S" (2,3-diethylthioxanthone manufactured by Nippon Kayaku Co., Ltd.) and "EAB-F" (4,4'-bis(diethylamino)benzophenone manufactured by Hodogaya Chemical Industry Co., Ltd.).

More specific examples include, but are not limited to, the sensitizers described in Shin Okawara et al., "Dye Handbook" (1986, Kodansha), Shin Okawara et al., "Chemistry of Functional Dyes" (1981, CMC), Chuzaburo Ikemori et al., and "Special Functional Materials" (1986, CMC). In addition, a sensitizer that absorbs light in the ultraviolet to near-infrared region can also be included.

The sensitizers can be used singly or as a mixture of two or more at any ratio as required.

The content when using a sensitizer is preferably 3 to 60 parts by weight with respect to 100 parts by weight of the photopolymerization initiator (C) contained in the coloring composition, and more preferably 5 to 50 parts by weight from the viewpoint of photocurability and developability.

[Resin (D)]
The photosensitive coloring composition of this embodiment contains a resin (D). The resin (D) is preferably a resin having a transmittance of preferably 80% or more, more preferably 95% or more in the entire wavelength range of 400 to 700 nm in the visible light region, from the viewpoint of the spectral characteristics of the pixel. The resin (D) includes thermoplastic resins, thermosetting resins, photosensitive resins, and pigment dispersion resins, and these can be used alone or in combination of two or more.

Examples of thermoplastic resins include butyral resins, styrene-maleic acid copolymers, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymers, polyvinyl acetate, polyurethane resins, polyester resins, acrylic resins, alkyd resins, polystyrene, polyamide resins, rubber resins, cyclized rubber resins, celluloses, polyethylene, polybutadiene, polyimide resins, and the like.

Examples of thermosetting resins include epoxy resins, benzoguanamine resins, rosin-modified maleic acid resins, rosin-modified fumaric acid resins, melamine resins, urea resins, and phenolic resins.

As the photosensitive resin, a linear polymer having a reactive substituent such as a hydroxyl group, a carboxyl group, or an amino group is reacted with a (meth)acrylic compound or cinnamic acid having a reactive substituent such as an isocyanate group, an aldehyde group, or an epoxy group, and a resin obtained by introducing a photocrosslinkable group such as a (meth)acryloyl group or a styryl group into the linear polymer is used. In addition, a linear polymer containing an acid anhydride such as a styrene-maleic anhydride copolymer or an α-olefin-maleic anhydride copolymer is half-esterified with a (meth)acrylic compound having a hydroxyl group such as a hydroxyalkyl (meth)acrylate.

The photosensitive resin preferably has an ethylenically unsaturated bond. In particular, by using a resin into which an ethylenically unsaturated bond is introduced by the method (i) or (ii) shown below, the resin is three-dimensionally crosslinked when exposed to active energy rays to form a coating film, thereby increasing the crosslink density and improving chemical resistance.

<Method (i)>
As method (i), for example, there is a method in which an ethylenically unsaturated monomer having an epoxy group and a side chain epoxy group of a copolymer obtained by copolymerizing one or more other monomers are subjected to an addition reaction with a carboxyl group of an unsaturated monobasic acid having an ethylenically unsaturated bond, and a polybasic acid anhydride is reacted with the resulting hydroxyl group to introduce an ethylenically unsaturated bond and a carboxyl group.

Examples of ethylenically unsaturated monomers having an epoxy group include glycidyl (meth) acrylate, methyl glycidyl (meth) acrylate, 2-glycidoxyethyl (meth) acrylate, 3,4-epoxybutyl (meth) acrylate, and 3,4-epoxycyclohexyl (meth) acrylate. These may be used alone or in combination of two or more. Glycidyl (meth)acrylate is preferred from the viewpoint of reactivity with the unsaturated monobasic acid in the next step.

Examples of the unsaturated monobasic acid include (meth)acrylic acid, crotonic acid, o-, m-, p-vinylbenzoic acid, α-position haloalkyl, alkoxyl, halogen, nitro, and cyano-substituted monocarboxylic acids of (meth)acrylic acid, etc. These may be used alone or in combination of two or more.

Examples of polybasic acid anhydrides include tetrahydrophthalic anhydride, phthalic anhydride, hexahydrophthalic anhydride, succinic anhydride, and maleic anhydride. These may be used alone or in combination of two or more. If necessary, such as increasing the number of carboxyl groups, a tricarboxylic acid anhydride such as trimellitic anhydride can be used, or a tetracarboxylic acid dianhydride such as pyromellitic dianhydride can be used to hydrolyze the remaining anhydride groups. Moreover, when tetrahydrophthalic anhydride or maleic anhydride having an ethylenically unsaturated bond is used as the polybasic acid anhydride, the ethylenically unsaturated bond can be further increased.

As a method similar to the method (i), for example, there is a method of introducing an ethylenically unsaturated bond and a carboxyl group by subjecting an ethylenically unsaturated monomer having an epoxy group to a part of the side chain carboxyl groups of a copolymer obtained by copolymerizing an ethylenically unsaturated monomer having a carboxyl group with one or more other monomers.

<Method (ii)>
As method (ii), an ethylenically unsaturated monomer having a hydroxyl group is used, and an unsaturated monobasic acid monomer having another carboxyl group or a copolymer obtained by copolymerizing other monomers is used. The side chain hydroxyl group of the copolymer is reacted with the isocyanate group of the ethylenically unsaturated monomer having an isocyanate group.

Examples of ethylenically unsaturated monomers having a hydroxyl group include hydroxyalkyl methacrylates such as 2-hydroxyethyl (meth) acrylate, 2- or 3-hydroxypropyl (meth) acrylate, 2- or 3- or 4-hydroxybutyl (meth) acrylate, glycerol mono (meth) acrylate, or cyclohexanedimethanol mono (meth) acrylate, and these may be used alone or in combination of two or more. In addition, polyether mono(meth)acrylate obtained by addition polymerization of ethylene oxide, propylene oxide, and/or butylene oxide, etc., to the above hydroxyalkyl (meth)acrylate, and polyester mono(meth)acrylate obtained by adding poly γ-valerolactone, poly ε-caprolactone, and/or poly 12-hydroxystearic acid, etc. can also be used. From the viewpoint of suppressing coating film foreign substances, 2-hydroxyethyl methacrylate or glycerol mono (meth) acrylate is preferable, and from the viewpoint of sensitivity, it is preferable to use those having 2 to 6 hydroxyl groups, and glycerol mono (meth) acrylate is more preferable.

Examples of the ethylenically unsaturated monomer having an isocyanate group include 2-(meth)acryloylethyl isocyanate, 2-(meth)acryloyloxyethyl isocyanate, or 1,1-bis[methacryloyloxy]ethyl isocyanate.

Examples of monomers constituting the alkali-soluble resin include the following. Methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, cyclohexyl (meth) acrylate, stearyl (meth) acrylate, lauryl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, isobornyl (meth) acrylate, phenyl (meth) acrylate, benzyl (meth) acrylate, phenoxyethyl (meth) ) acrylates, phenoxydiethylene glycol (meth)acrylate, methoxypolypropylene glycol (meth)acrylate, ethoxypolyethylene glycol (meth)acrylates; (meth)acrylamides, N,N-dimethyl (meth)acrylamide, N,N-diethyl (meth)acrylamide, N-isopropyl (meth)acrylamide, diacetone (meth)acrylamide, acryloylmorpholine and other (meth)acrylamides; styrene, α-methylstyrene and other styrenes; ethyl vinyl ether, n-propyl vinyl ether, vinyl ethers such as isopropyl vinyl ether, n-butyl vinyl ether and isobutyl vinyl ether; fatty acid vinyls such as vinyl acetate and vinyl propionate; 3-ethyl-5-methyl-4-maleimidophenyl)methane, N,N'-1,3-phenylenedimaleimide, N,N'-1,4-phenylenedimaleimide, N-(1-pyrenyl)maleimide, N-(2,4,6-trichlorophenyl)maleimide, N-(4-aminophenyl)maleimide, N-(4-nitrophenyl)maleimide, N-benzylmaleimide, N-bromomethyl-2,3-dichloromaleimide N-substituted maleimides such as amide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-3-maleimidopropionate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidohexanoate, N-[4-(2-benzimidazolyl)phenyl]maleimide, 9-maleimidoacridine, and compounds represented by the following general formula (6) is mentioned.

（一般式（６）中、Ｒ^５１は、水素原子、又はメチル基であり、Ｒ^５２は、炭素数２～３のアルキレン基であり、Ｒ^５３は、ベンゼン環を有していてもよい炭素数１～２０のアルキル基であり、ｎは、１～１５の整数である。）

(In general formula (6), R ⁵¹ is a hydrogen atom or a methyl group, R ⁵² is an alkylene group having 2 to 3 carbon atoms, R ⁵³ is an alkyl group having 1 to 20 carbon atoms which may have a benzene ring, and n is an integer of 1 to 15.)

Specific examples of the compound represented by the following general formula (6) include EO-modified cresol acrylate, n-nonylphenoxy polyethylene glycol acrylate, phenoxyethyl acrylate, ethoxylated phenyl acrylate, ethylene oxide (EO)-modified (meth)acrylate of phenol, EO- or propylene oxide (PO)-modified (meth)acrylate of paracumylphenol, EO-modified (meth)acrylate of nonylphenol, and PO-modified (meth)acrylate of nonylphenol.

Carboxyl group-containing ethylenically unsaturated monomers can also be used. Carboxyl group-containing ethylenically unsaturated monomers include, for example, acrylic acid, methacrylic acid, ε-caprolactone-added acrylic acid, ε-caprolactone-added methacrylic acid, itaconic acid, maleic acid, fumaric acid, and crotonic acid.

A hydroxyl group-containing ethylenically unsaturated monomer can also be used. Examples of hydroxyl group-containing ethylenically unsaturated monomers include 2-hydroxyethyl (meth) acrylate, 2- or 3-hydroxypropyl (meth) acrylate, 2- or 3- or 4-hydroxybutyl (meth) acrylate, and hydroxyalkyl (meth) acrylates such as cyclohexanedimethanol mono (meth) acrylate. Further examples include polyether mono(meth)acrylates obtained by addition polymerization of ethylene oxide, propylene oxide, and/or butylene oxide, etc., and (poly)ester mono(meth)acrylates obtained by adding (poly)γ-valerolactone, (poly)ε-caprolactone, and/or (poly)12-hydroxystearic acid to the above hydroxyalkyl (meth)acrylates.

Phosphate ester group-containing ethylenically unsaturated monomers can also be used. Examples of the phosphate ester group-containing ethylenically unsaturated monomers include monomers that can be obtained by reacting the hydroxyl groups of the hydroxyl group-containing ethylenically unsaturated monomers with a phosphate esterifying agent such as phosphorus pentoxide and polyphosphoric acid.

In this implementation, the resin (D) preferably contains a photosensitive resin. By containing a photosensitive resin, there is an effect of improving chemical resistance and solvent resistance after curing the colored composition.

<Photosensitive resin (E)>
The photosensitive resin (E) is a hydroxyl group-containing polymer obtained by polymerizing an ethylenically unsaturated monomer (c) containing a hydroxyl group-containing ethylenically unsaturated monomer (b) in the presence of a reaction product of a compound (a) having two hydroxyl groups and one thiol group in the molecule and an acid anhydride group of pyromellitic anhydride and/or trimellitic anhydride. It is a resin obtained by reacting the isocyanate group of the compound (d) having an yl group, and the content of structural units derived from the hydroxyl group-containing ethylenically unsaturated monomer (b) is preferably 35% by mass or more and 80% by mass or less with respect to the total amount of structural units derived from the ethylenically unsaturated monomer (c).
By containing the photosensitive resin (E), there is an effect of further improving chemical resistance and solvent resistance after curing the colored composition.

The photosensitive resin (E) is prepared by first producing a reaction product of the hydroxyl group of compound (a) having two hydroxyl groups and one thiol group and the acid anhydride group of pyromellitic anhydride and/or trimellitic anhydride, followed by radical polymerization of the ethylenically unsaturated monomer (c) containing the hydroxyl group-containing ethylenically unsaturated monomer (b) using the remaining thiol group of the reaction product as a chain transfer agent to carry out vinyl polymerization having a hydroxyl group. It is obtained by going through a second step of producing a hydroxyl group-containing polymer into which a moiety is introduced, and a third step of reacting one isocyanate group with a compound (d) having one or more (meth)acryloyl groups. A plurality of carboxyl group moieties in the photosensitive resin (E) function as pigment adsorption moieties, and vinyl polymer moieties function as solvent affinity moieties.

Further, the photosensitive resin (E) has a structure obtained through a plurality of reactions such as a reaction between a hydroxyl group and an acid anhydride group, a radical polymerization reaction using a residual thiol group as a chain transfer agent, and a reaction between a residual hydroxyl group and an isocyanate group. Since the photosensitive resin (E) has a complicated structure, hereinafter, the photosensitive resin (E) will be specified according to the manufacturing method.

(Compound (a) having two hydroxyl groups and one thiol group in the molecule)
As the compound (a) having two hydroxyl groups and one thiol group in the molecule, 3-mercapto-1,2-propanediol (also known as 1-thioglycerol) can be preferably used.

A well-known catalyst can be used as a catalyst used when reacting an acid anhydride group and a hydroxyl group. Examples include triethylamine, triethylenediamine, N,N-dimethylbenzylamine, N-methylmorpholine, 1,8-diazabicyclo-[5.4.0]-7-undecene, 1,5-diazabicyclo-[4.3.0]-5-nonene, monobutyltin oxide and the like.

Next, a second step of producing a hydroxyl group-containing polymer into which a hydroxyl group-containing ethylenically unsaturated monomer is introduced by radically polymerizing the ethylenically unsaturated monomer (c) containing the hydroxyl group-containing ethylenically unsaturated monomer (b) using the thiol group remaining in the reaction product of the hydroxyl group of the compound (a) having two hydroxyl groups and one thiol group and the acid anhydride group of pyromellitic anhydride and/or trimellitic anhydride as a chain transfer agent will be described. . By copolymerizing the ethylenically unsaturated monomer (b) containing a hydroxyl group in the second step, a hydroxyl group can be introduced into the vinyl polymer portion of the dispersant, and in the third step, it can be reacted with the compound (d) having one isocyanate group and one or more (meth)acryloyl groups.

(Hydroxyl group-containing ethylenically unsaturated monomer (b))
The hydroxyl group-containing ethylenically unsaturated monomer (b) may be any monomer as long as it has a hydroxyl group and an ethylenically unsaturated bond. Specifically, a (meth)acrylate monomer having a hydroxyl group, such as 2-hydroxyethyl (meth) acrylate, 2 (or 3)-hydroxypropyl (meth) acrylate, 2 (or 3 or 4)-hydroxybutyl (meth) acrylate and hydroxyalkyl (meth) acrylates such as cyclohexanedimethanol mono (meth) acrylate, and ethyl-α- Alkyl-α-hydroxyalkyl acrylates such as hydroxymethyl acrylate, or (meth)acrylamide-based monomers having a hydroxyl group, such as N-(2-hydroxyethyl)(meth)acrylamide, N-(2-hydroxypropyl)(meth)acrylamide, N-(2-hydroxybutyl)(meth)acrylamide, etc., or vinyl ether-based monomers having a hydroxyl group, such as 2-hydroxyethyl vinyl ether, 2-(or 3-)hydroxypropyl vinyl ether, 2- (or 3- or 4-) hydroxyalkyl vinyl ethers such as hydroxybutyl vinyl ether, or allyl ether monomers having a hydroxyl group, such as 2-hydroxyethyl allyl ether, 2- (or 3-) hydroxypropyl allyl ether, 2- (or 3- or 4-) hydroxyalkyl allyl ethers such as hydroxybutyl allyl ether.

(Other ethylenically unsaturated monomers)
Examples of ethylenically unsaturated monomers other than the hydroxyl group-containing ethylenically unsaturated monomer (b) include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, cyclohexyl (meth)acrylate, 2,2,4-trimethylcyclohexyl (meth)acrylate, and stearyl (meth)acrylate. , Alkyl (meth)acrylates such as lauryl (meth)acrylate and isobornyl (meth)acrylate; aromatic (meth)acrylates such as phenyl (meth)acrylate, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, and phenoxydiethylene glycol (meth)acrylate; heterocyclic (meth)acrylates such as tetrahydrofurfuryl (meth)acrylate; (N-substituted) (meth)acrylamides such as -dimethyl (meth)acrylamide, N,N-diethyl (meth)acrylamide, N-isopropyl (meth)acrylamide, diacetone (meth)acrylamide, and acryloylmorpholine; amino group-containing (meth)acrylates such as N,N-dimethylaminoethyl (meth)acrylate and N,N-diethylaminoethyl (meth)acrylate; and nitriles such as (meth)acrylonitrile.

Examples of the monomer that can be used in combination with the acrylic monomer include styrenes such as styrene, α-methylstyrene and indene, vinyl ethers such as ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether and isobutyl vinyl ether, and fatty acid vinyls such as vinyl acetate and vinyl propionate.

A carboxyl group-containing ethylenically unsaturated monomer can also be used in combination. As the carboxyl group-containing ethylenically unsaturated monomer, one or more of acrylic acid, methacrylic acid, itaconic acid, maleic acid, fumaric acid, crotonic acid and the like can be selected.

The content of the hydroxyl group-containing ethylenically unsaturated monomer (b) is desirably 35% by mass or more and 80% by mass or less with respect to the total amount of the ethylenically unsaturated monomers (c).

Next, the third step of reacting the hydroxyl group-containing compound with the compound (d) having one isocyanate group and one or more (meth)acryloyl groups will be described. The photosensitive resin is obtained by reacting a hydroxyl group in the hydroxyl group-containing compound with an isocyanate group in the compound (d) having one isocyanate group and one or more (meth)acryloyl groups. As a result, a (meth)acryloyl group can be arbitrarily introduced mainly into the vinyl polymer portion in the dispersant, and a photosensitive resin having curable properties in the solvent affinity portion can be obtained.

(Compound (d) having one isocyanate group and one or more (meth)acryloyl groups)
The compound (d) having one isocyanate group and one or more (meth)acryloyl groups used in the third step is preferably a compound having one isocyanate group and one or two (meth)acryloyl groups, specifically 2-methacryloyloxyethyl isocyanate and 2-acryloyloxyethyl isocyanate.

The compound (d) having one isocyanate group and one or more (meth)acryloyl groups used in this embodiment is not limited to the compounds exemplified above, and may have any structure as long as it has an isocyanate group and one or more (meth)acryloyl groups. These may be used alone or in combination.

A resin having an oxetane group can also be used as the resin (D). A resin having an oxetane group can be obtained, for example, by copolymerizing an ethylenically unsaturated monomer having an oxetane group. Examples of ethylenically unsaturated monomers having an oxetane group include (3-methyl-3-oxetanyl)methyl (meth)acrylate, (3-ethyl-3-oxetanyl)methyl (meth)acrylate, (3-butyl-3-oxetanyl)methyl (meth)acrylate, (3-hexyltyl-3-oxetanyl)methyl (meth)acrylate and the like.
Examples of commercially available products include ETERNACOLL OXMA (manufactured by Ube Industries, Ltd.), OXE-10, and OXE-30 (manufactured by Osaka Organic Chemical Industry Co., Ltd.).
Since the resin has an oxetane group, the colored composition containing the resin has excellent heat resistance after curing.

The resin (D) can be used in an amount of 1 to 400 parts by weight, preferably 1 to 300 parts by weight, per 100 parts by weight of the colorant (A) in the photosensitive coloring composition.

[Antioxidant]
The photosensitive coloring composition of this embodiment may contain an antioxidant. The antioxidant prevents the photopolymerization initiator and the thermosetting compound from being oxidized and yellowing due to the heat process during thermosetting and ITO annealing, so that the transmittance of the pixel can be increased.

The "antioxidant" in the present embodiment may be a compound having an ultraviolet absorption function, a radical scavenging function, or a peroxide decomposition function. Specifically, the antioxidant includes hindered phenol-based, hindered amine-based, phosphorus-based, sulfur-based, benzotriazole-based, benzophenone-based, hydroxylamine-based, salicylic acid ester-based, and triazine-based compounds, and known ultraviolet absorbers, antioxidants, and the like can be used.

Among these antioxidants, hindered phenol-based antioxidants, hindered amine-based antioxidants, phosphorus-based antioxidants, or sulfur-based antioxidants are preferable, and hindered phenol-based antioxidants, hindered amine-based antioxidants, or phosphorus-based antioxidants are more preferable, from the viewpoint of achieving both transmittance and sensitivity of the coating film.

Hindered phenol antioxidants include 2,4-bis[(laurylthio)methyl]-o-cresol, 1,3,5-tris(3,5-di-t-butyl-4-hydroxybenzyl), 1,3,5-tris(4-t-butyl-3-hydroxy-2,6-dimethylbenzyl), 2,4-bis-(n-octylthio)-6-(4-hydroxy-3,5-di-t-butylanilino)-1,3 ,5-triazine, pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, 2,6-di-t-butyl-4-nonylphenol, 2,2'-isobutylidene-bis-(4,6-dimethyl-phenol), 4,4'-butylidene-bis-(2-t-butyl-5-methylphenol), 2,2'-thio-bis-(6-t-butyl-4-methylphenol), 2 ,5-di-t-amyl-hydroquinone, 2,2' thiodiethylbis-(3,5-di-t-butyl-4-hydroxyphenyl)-propionate, 1,1,3-tris-(2'-methyl-4'-hydroxy-5'-t-butylphenyl)-butane, 2,2'-methylene-bis-(6-(1-methyl-cyclohexyl)-p-cresol), 2,4-dimethyl-6-(1-methyl-cyclohexyl )-phenol, N,N-hexamethylenebis(3,5-di-t-butyl-4-hydroxy-hydrocinnamamide) and the like. In addition, oligomer type and polymer type compounds having a hindered phenol structure can also be used.

Hindered amine antioxidants include bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis(N-methyl-2,2,6,6-tetramethyl-4-piperidyl) sebacate, N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)-1,6-hexamethylenediamine, 2-methyl-2-(2,2,6,6-tetramethyl-4-piperidyl) Amino-N-(2,2,6,6-tetramethyl-4-piperidyl)propionamide, tetrakis(2,2,6,6-tetramethyl-4-piperidyl)(1,2,3,4-butanetetracarboxylate), poly[{6-(1,1,3,3-tetramethylbutyl)imino-1,3,5-triazine-2,4-diyl}{(2,2,6,6-tetramethyl-4-piperidyl)imino}hexamethyl {(2,2,6,6-tetramethyl-4-piperidyl)imino}], poly[(6-morpholino-1,3,5-triazine-2,4-diyl){(2,2,6,6-tetramethyl-4-piperidyl)imino}hexamethine {(2,2,6,6-tetramethyl-4-piperidyl)imino}], dimethyl succinate and 1-(2-hydroxyethyl)-4-hydroxy-2,2,6 ,6-tetramethylpiperidine polycondensate, N,N′-4,7-tetrakis[4,6-bis{N-butyl-N-(1,2,2,6,6-pentamethyl-4-piperidyl)amino}-1,3,5-triazin-2-yl]-4,7-diazadecane-1,10-diamine, etc. In addition, oligomer type and polymer type compounds having a hindered amine structure may also be used.

Phosphorus-based antioxidants include tris(isodecyl)phosphite, tris(tridecyl)phosphite, phenylisooctylphosphite, phenylisodecylphosphite, phenyldi(tridecyl)phosphite, diphenylisooctylphosphite, diphenylisodecylphosphite, diphenyltridecylphosphite, triphenylphosphite, tris(nonylphenyl)phosphite, 4,4' isopropyl Dendiphenol alkyl phosphite, trisnonylphenyl phosphite, trisdinonylphenyl phosphite, tris(2,4-di-t-butylphenyl) phosphite, tris(biphenyl) phosphite, distearyl pentaerythritol diphosphite, di(2,4-di-t-butylphenyl) pentaerythritol diphosphite, di(nonylphenyl) pentaerythritol diphosphite, phenylbisphenol A pentaeryth lithol diphosphite, tetratridecyl 4,4'-butylidenebis(3-methyl-6-t-butylphenol) diphosphite, hexatridecyl 1,1,3-tris(2-methyl-4-hydroxy-5-t-butylphenyl)butane triphosphite, 3,5-di-t-butyl-4-hydroxybenzylphosphite diethyl ester, sodium bis(4-t-butylphenyl)phosphite, sodium-2,2-methylene-bis (4,6-di-t-butylphenyl)-phosphite, 1,3-bis(diphenoxyphosphonyloxy)-benzene, ethylbis(2,4-di-tert-butyl-6-methylphenyl) phosphite and the like. In addition, oligomer type and polymer type compounds having a phosphite structure may also be used.

Sulfur antioxidants include 2,2-thio-diethylenebis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], 2,4-bis[(octylthio)methyl]-o-cresol, 2,4-bis[(laurylthio)methyl]-o-cresol and the like. In addition, oligomer type and polymer type compounds having a thioether structure may also be used.

Examples of benzotriazole-based antioxidants include oligomer-type and polymer-type compounds having a benzotriazole structure.

Benzophenone antioxidants such as 2-hydroxy-4-methoxybenzophenone, 2,4-dihydroxybenzophenone, 2-hydroxy-4-n-octoxybenzophenone, 4-dodecyloxy-2-hydroxybenzophenone, 2-hydroxy-4-octadecyloxybenzophenone, 2,2'dihydroxy-4-methoxybenzophenone, 2,2'dihydroxy-4,4'-dimethoxybenzophenone, 2,2',4,4'-tetrahydroxybenzophenone , 2-hydroxy-4-methoxy-5sulfobenzophenone, 2-hydroxy-4-methoxy-2'-carboxybenzophenone, 2-hydroxy-4-chlorobenzophenone and the like. In addition, oligomer type and polymer type compounds having a benzophenone structure may also be used.

Triazine-based antioxidants include 2,4-bis(allyl)-6-(2-hydroxyphenyl)1,3,5-triazine and the like. In addition, oligomer type and polymer type compounds having a triazine structure may also be used.

Salicylic acid ester-based antioxidants include phenyl salicylate, p-octylphenyl salicylate, p-tertbutylphenyl salicylate, and the like. In addition, oligomer type and polymer type compounds having a salicylic acid ester structure may also be used.

These antioxidants can be used singly or as a mixture of two or more at any ratio as required.

Moreover, the content of the antioxidant is preferably 0.5 to 5.0% by mass based on the total solid content of the photosensitive coloring composition from the viewpoint of brightness and sensitivity.

[Adhesion improver]
The photosensitive coloring composition may contain an adhesion improver such as a silane coupling agent in order to improve adhesion to the substrate. By improving the adhesion with the adhesion improving agent, the reproducibility of fine lines is improved and the resolution is improved.

Examples of the adhesion improver include vinylsilanes such as vinyltrimethoxysilane and vinyltriethoxysilane; Epoxysilanes such as 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N-(1,3-dimethyl-butylidene)propylamine, N- Aminosilanes such as phenyl-3-aminopropyltrimethoxysilane and hydrochloride of N-(vinylbenzyl)-2-aminoethyl-3-aminopropyltrimethoxysilane; mercaptos such as 3-mercaptopropylmethyldimethoxysilane and 3-mercaptopropyltrimethoxysilane; styryls such as p-styryltrimethoxysilane; Examples include silane coupling agents such as isocyanates such as propyltriethoxysilane. The adhesion improver can be used in an amount of 0.01 to 10 parts by weight, preferably 0.05 to 5 parts by weight, per 100 parts by weight of the colorant in the coloring composition. Within this range, the effect is enhanced and the balance between adhesion, resolution, and sensitivity is good, which is more preferable.

[Leveling agent]
A leveling agent may be added to the photosensitive coloring composition in order to improve the leveling properties of the composition. As the leveling agent, dimethylsiloxane having a polyether structure or a polyester structure in its main chain is preferred. Specific examples of dimethylsiloxane having a polyether structure in the main chain include FZ-2122 manufactured by Dow Corning Toray Co., Ltd. and BYK-333 manufactured by BYK Chemie. Specific examples of dimethylsiloxane having a polyester structure include BYK-310 and BYK-370 manufactured by BYK-Chemie. A dimethylsiloxane having a polyether structure in its main chain and a dimethylsiloxane having a polyester structure in its main chain can be used in combination. The content of the leveling agent is preferably 0.003 to 0.5% by mass based on the total solid content of the coloring composition.

Especially preferred as a leveling agent is a type of so-called surfactant having a hydrophobic group and a hydrophilic group in the molecule, which has a hydrophilic group but has low solubility in water, and when added to a coloring composition, has the characteristics of low surface tension lowering ability, has good wettability to a glass plate in spite of its low surface tension lowering ability, is useful, and can sufficiently suppress electrification in an amount that does not cause defects in the coating film due to bubbling. Dimethylpolysiloxane having polyalkylene oxide units can be preferably used as a leveling agent having such preferred properties. Polyalkylene oxide units include polyethylene oxide units and polypropylene oxide units, and dimethylpolysiloxane may have both polyethylene oxide units and polypropylene oxide units.

Anionic, cationic, nonionic or amphoteric surfactants can be added to the leveling agent as auxiliaries. Two or more kinds of surfactants may be mixed and used.
Examples of the anionic surfactant that is added to the leveling agent include polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium alkyl naphthalene sulfonate, sodium alkyldiphenyl ether disulfonate, monoethanolamine lauryl sulfate, triethanolamine lauryl sulfate, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymer, and polyoxyethylene alkyl ether phosphate.

Cationic surfactants added to the leveling agent include alkyl quaternary ammonium salts and their ethylene oxide adducts. Examples of nonionic surfactants that are added to the leveling agent include amphoteric surfactants such as polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate, polyoxyethylene sorbitan monostearate, polyethylene glycol monolaurate; alkylbetaines such as alkyldimethylaminoacetic acid betaine; and alkylimidazoline.

[Curing agent, curing accelerator]
Moreover, the photosensitive coloring composition may contain a curing agent and a curing accelerator as necessary in order to assist curing of the thermosetting resin. Phenol-based resins, amine-based compounds, acid anhydrides, active esters, carboxylic acid-based compounds, sulfonic acid-based compounds, and the like are effective as curing agents, but are not particularly limited to these, and any curing agent may be used as long as it can react with the thermosetting resin. Among these, compounds having two or more phenolic hydroxyl groups in one molecule and amine curing agents are preferred. Examples of the curing accelerator include amine compounds (e.g., dicyandiamide, benzyldimethylamine, 4-(dimethylamino)-N,N-dimethylbenzylamine, 4-methoxy-N,N-dimethylbenzylamine, 4-methyl-N,N-dimethylbenzylamine, etc.), quaternary ammonium salt compounds (e.g., triethylbenzylammonium chloride, etc.), blocked isocyanate compounds (e.g., dimethylamine, etc.), imidazole derivative bicyclic amidine compounds and salts thereof (e.g., imidazole, 2-methylimidine). dazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 4-phenylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-(2-cyanoethyl)-2-ethyl-4-methylimidazole, etc.), phosphorus compounds (e.g., triphenylphosphine, etc.), guanamine compounds (e.g., melamine, guanamine, acetoguanamine, benzoguanamine, etc.), S-triazine derivatives (e.g., 2,4-diamino-6-methacryloyloxyethyl-S-triazine, 2-vinyl-2,4-diamino-S-triazine, 2-vinyl-4,6-diamino-S-triazine/isocyanuric acid adduct, 2,4-diamino-6-methacryloyloxyethyl-S-triazine/isocyanuric acid adduct, etc.) can be used. These may be used individually by 1 type, and may use 2 or more types together. The content of the curing accelerator is preferably 0.01 to 15 parts by mass with respect to 100 parts by mass of the thermosetting resin.

[Storage stabilizer]
The photosensitive coloring composition of this embodiment may contain a storage stabilizer in order to stabilize the viscosity over time.
Examples of storage stabilizers include benzyltrimethyl chloride, quaternary ammonium chloride such as diethylhydroxyamine, organic acids such as lactic acid and oxalic acid and their methyl ethers, organic phosphines such as t-butylpyrocatechol, tetraethylphosphine and tetraphenylphosphine, and phosphites. The storage stabilizer can be used in an amount of 0.1 to 10 parts by weight with respect to 100 parts by weight of the colorant.

[solvent]
In addition, the photosensitive coloring composition may contain a solvent in order to sufficiently disperse and permeate the coloring agent into the coloring agent carrier to facilitate formation of a coating film. The solvent is selected in consideration of good applicability of the photosensitive coloring composition, solubility of each component of the photosensitive composition, and safety.

Examples of solvents include 1,2,3-trichloropropane, 1-methoxy-2-propanol, ethyl lactate, 1,3-butanediol, 1,3-butylene glycol, 1,3-butylene glycol diacetate, 1,4-butanediol diacetate, 1,4-dioxane, 2-heptanone, 2-methyl-1,3-propanediol, 3,5,5-trimethyl-2-cyclohexene-1-one, 3 , 3,5-trimethylcyclohexanone, ethyl 3-ethoxypropionate, 3-methyl-1,3-butanediol, 3-methoxy-3-methyl-1-butanol, 3-methoxy-3-methylbutyl acetate, 3-methoxybutanol, 3-methoxybutyl acetate, 4-heptanone, m-xylene, m-diethylbenzene, m-dichlorobenzene, N,N-dimethylacetamide, N,N-dimethylformamide, n-butyl alcohol, n -butylbenzene, n-propyl acetate, N-methylpyrrolidone, o-xylene, o-chlorotoluene, o-diethylbenzene, o-dichlorobenzene, p-chlorotoluene, p-diethylbenzene, sec-butylbenzene, tert-butylbenzene, γ-butyrolactone, isobutyl alcohol, isophorone, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monotertiary butyl ether, Ethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate, ethylene glycol monopropyl ether, ethylene glycol monohexyl ether, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, diisobutyl ketone, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether, diethylene glycol monobutyl ether acetate, diethylene glycol monomethyl ether, cyclohexanol, cyclohexanol acetate, cyclohexanol acetate non, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether acetate, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monomethyl ether, diacetone alcohol, triacetin, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol diacetate, propylene glycol phenyl ether, propylene glycol monoethyl ether, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether, propylene glycol monopropyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate , propylene glycol monomethyl ether propionate, benzyl alcohol, methyl isobutyl ketone, methylcyclohexanol, n-amyl acetate, n-butyl acetate, isoamyl acetate, isobutyl acetate, propyl acetate, dibasic acid esters, and the like.
These solvents can be used singly or as a mixture of two or more at any ratio as required.

Among them, acetates such as ethyl lactate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol diacetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, 1,3-butylene glycol diacetate, cyclohexanol acetate, 1,4-butanediol diacetate, butanediol diacetate, etc. are preferred because of their good dispersibility and permeability of colorants and applicability of photosensitive compositions. It is preferable to use alcohols such as triglycerides, benzyl alcohol, diacetone alcohol, 1-methoxy-2-propanol and 3-methoxybutanol, ketones such as cyclohexanone, ethyl 3-ethoxypropionate, and the like.

In addition, since these solvents can adjust the viscosity of the photosensitive coloring composition to an appropriate viscosity and form a coating film having the desired uniform thickness, it is preferable to use them in an amount of 500 to 4000 parts by weight with respect to 100 parts by weight of the coloring agent.

[Dispersing aid]
When the colorant is dispersed in the colorant carrier, a dispersing aid such as a pigment derivative, a resin-type dispersant, or a surfactant may be contained as appropriate. Since the dispersing aid has a great effect of preventing reaggregation of the colorant after dispersion, the coloring composition obtained by dispersing the colorant in the colorant carrier using the dispersing aid has good brightness and viscosity stability.

<Dye derivative>
Examples of dye derivatives include organic pigments, anthraquinones, acridones or triazines, and compounds obtained by introducing a basic substituent, an acidic substituent, or a phthalimidomethyl group optionally having a substituent. 2001-335717, JP 2003-128669, JP 2004-091497, JP 2007-156395, JP 2008-094873, JP 2008-094986, JP 2008-095007, JP 2008-195916, Patent No. 45 Those described in JP-A-85781 and the like can be used, and these can be used alone or in combination of two or more.

The content of the pigment derivative is preferably 0.5 parts by mass or more, more preferably 1 part by mass or more, and most preferably 3 parts by mass or more with respect to 100 parts by mass of the colorant, from the viewpoint of improving dispersibility. From the viewpoint of heat resistance and light resistance, the amount is preferably 40 parts by mass or less, more preferably 35 parts by mass or less.

<Resin Dispersant>
The resin-type dispersant has a colorant affinity site having a property of adsorbing to the colorant and a site compatible with the colorant carrier, and acts to adsorb to the colorant and stabilize the dispersion of the colorant to the colorant carrier. Specific examples of resin-type dispersants include polycarboxylic acid esters such as polyurethanes and polyacrylates, unsaturated polyamides, polycarboxylic acids, polycarboxylic acid (partial) amine salts, polycarboxylic acid ammonium salts, polycarboxylic acid alkylamine salts, polysiloxanes, long-chain polyaminoamide phosphates, hydroxyl group-containing polycarboxylic acid esters, modified products thereof, amides formed by the reaction of poly(lower alkyleneimine) and polyesters having free carboxyl groups, and oily dispersants such as salts thereof, and (meth)acrylic acid-styrene copolymerization. Polymers, (meth)acrylic acid-(meth)acrylic acid ester copolymers, styrene-maleic acid copolymers, polyvinyl alcohol, water-soluble resins and water-soluble polymer compounds such as polyvinylpyrrolidone, polyesters, modified polyacrylates, ethylene oxide/propylene oxide addition compounds, phosphoric acid esters, etc. are used, and these can be used alone or in combination of two or more, but are not necessarily limited to these.

Commercially available resin-type dispersants include Disperbyk-101, 103, 107, 108, 110, 111, 116, 130, 140, 154, 161, 162, 163, 164, 165, 166, 170, 171, 174, 180, 181, 182, 183, 184 manufactured by BYK-Chemie Japan, 185, 190, 2000, 2001, 2020, 2025, 2050, 2070, 2095, 2150, 2155, or Anti-Terra-U, 203, 204, or BYK-P104, P104S, 220S, 6919, or Lactimon, Lactimon-WS or Bykumen etc., SOLSPERSE-3000, 9000, 13000, 13240, 13650, 13940, 16000, 17000, 18000, 20000, 21000, 24000, 26000, 27000, 28000, 31845, 32000, 32500, 3 manufactured by Nippon Lubrizol Co., Ltd. 2550, 33500, 32600, 34750, 35100, 36600, 38500, 41000, 41090, 53095, 55000, 76500, etc. EFKA-46, 47, 48, 452, 4008, 4009, 4010, 4015, 4020, 4 manufactured by BASF 047, 4050, 4055, 4060, 4080, 4400, 4401, 4402, 4403, 4406, 4408, 4300, 4310, 4320, 4330, 4340, 450, 451, 453, 4540, 4550, 4560, 4800, 5010, 5065, 50 66, 5070, 7500, 7554, 1101, 120, 150, 1501, 1502, 1503;

<Surfactant>
Surfactants include sodium lauryl sulfate, polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium stearate, sodium alkylnaphthalene sulfonate, sodium alkyldiphenyl ether disulfonate, monoethanolamine lauryl sulfate, triethanolamine lauryl sulfate, ammonium lauryl sulfate, monoethanolamine stearate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate; nonionic surfactants such as ethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate, polyoxyethylene sorbitan monostearate, polyethylene glycol monolaurate; cationic surfactants such as alkyl quaternary ammonium salts and their ethylene oxide adducts; not a thing

When a resin-type dispersant or surfactant is added, it is preferably 0.1 to 55 parts by mass, more preferably 0.1 to 45 parts by mass, per 100 parts by mass of the colorant. If the amount of the resin-type dispersant and surfactant is less than 0.1 parts by mass, it is difficult to obtain the effect of addition.

[Method for producing a photosensitive coloring composition]
A method for producing a photosensitive coloring composition includes, for example, a method of first preparing a colorant dispersion, and then adding a photopolymerizable monomer, a photopolymerization initiator, and optionally other components.
The colorant dispersion can be prepared, for example, by finely dispersing the colorant in a colorant carrier such as a binder resin and/or an organic solvent, preferably together with a dispersing aid, using various dispersing means such as a kneader, two-roll mill, three-roll mill, ball mill, horizontal sand mill, vertical sand mill, annular bead mill, or attritor. When the colorant (A) contains two or more colorants, the plurality of colorants may be dispersed in the colorant carrier at the same time, or the colorant dispersions may be separately prepared and then mixed. In addition, when the colorant has high solubility, specifically, when the colorant has high solubility in the organic solvent to be used, and when it is dissolved by stirring and no foreign matter is confirmed, it is not necessary to finely disperse and manufacture as described above.

<Removal of coarse particles>
Coarse particles of 5 μm or more, preferably 1 μm or more, more preferably 0.5 μm or more, particularly preferably 0.3 μm or more, and mixed dust are preferably removed from the slow-release coloring composition of the present embodiment by means of centrifugation, filtration with a sintered filter, membrane filter, or the like.

2. Organic EL Display Device Next, the configuration of an organic EL display device will be described with reference to FIG. FIG. 1 is a schematic cross-sectional view of the organic EL display device of this embodiment. The organic EL display device 10 of the present embodiment has an organic EL layer 2 and a color filter on a silicon substrate 1 on which drive elements are formed. If necessary, the color filter 3 may further have a sealing layer 4 or a cover glass 5, and may have a flat layer (planar) between the organic EL layer 2 and the color filter 3 (not shown).
Details of each configuration of the organic EL display device will be described below.

[Color filter]
In this embodiment, the color filter 3 is formed on the organic EL layer and includes at least red pixels, green pixels and blue pixels (3a, 3b, 3c). The pixel is a cured product of the photosensitive coloring composition described above. In this implementation, the color filter may further have magenta pixels, cyan pixels, yellow pixels, or other pixels.

<Manufacturing method of color filter>
In this embodiment, the color filters are formed on the organic EL layer 2 or on a flat layer provided as necessary. By providing the planarization layer, the fine uneven surface of the organic EL layer can be planarized.
A well-known curable resin can be used for the flat layer, preferably an ultraviolet curable resin, and if necessary, a thermosetting resin may be used together. Although the ultraviolet curable resin is not particularly limited, an acrylic resin exhibiting sensitivity to the i-line (wavelength of 365 nm) is preferable.

Although the method of forming the pixels constituting the color filter is not particularly limited, the following method can be used, for example.
First, the photosensitive coloring composition described above is applied to the organic EL layer or flat layer using a coating method such as a spray coating method, a dip coating method, a bar coating method, a call coating method, or a spin coating method to form a coating film.
Next, after drying the coating film as necessary, it is exposed through a mask of a predetermined pattern to photopolymerize a photopolymerizable monomer or a photosensitive resin to form a cured coating film. Light sources used for exposure include, for example, ultraviolet light from low-pressure mercury lamps, high-pressure mercury lamps, metal halide lamps, electron beams, and the like. The amount of exposure may be appropriately adjusted depending on the light source used, the thickness of the coating film, and the like.
Moreover, in order to accelerate the polymerization reaction after exposure, heat treatment may be performed. Since the photosensitive composition has low-temperature curability, it can be sufficiently cured even by heat treatment at 100° C. or less.

In this embodiment, the film thickness of the pixels forming the color filter is 1.0 μm to 2.0 μm.
Further, the red pixels, green pixels, and blue pixels that constitute the color filter in this embodiment have the following spectral characteristics, so that a high-quality organic EL display device having high luminance and high color reproducibility can be obtained.
Red pixel: The maximum transmittance of light in the wavelength range of 450 nm to 560 nm is 0.4% or less, and the transmittance of light in the wavelength range of 600 nm to 700 nm is 80% or more and less than 100%.
Green pixel: The maximum transmittance of light in the wavelength range of 400 nm to 470 nm is 2% or less, the transmittance of light of 520 nm wavelength is 70% or more, and the transmittance of light of 550 nm wavelength is 60% or less.
Blue pixel: maximum transmittance of light in the wavelength range of 500 nm to 560 nm is less than 20%.
Since each pixel of the color filter of this embodiment has the above spectral characteristics, the color filter has a wide color gamut.

[Organic EL layer]
The organic EL layer can be formed of an organic light-emitting single layer or multiple layers containing a light-emitting material. When formed in multiple layers, for example, a general three-layer structure in which a hole-transporting layer, an electron-transporting organic light-emitting layer, and an electron-transporting layer are sequentially laminated, or a multilayer structure in which a hole (electron) injection layer and a hole (electron) transport layer are provided with separate layers for injection and transport functions, or a layer for blocking hole (electron) transport may be provided.

An example of the organic EL layer is a structure in which an anode, an organic layer, and a cathode are laminated in order from the silicon substrate side, and airtightly covered with a sealing layer.

The anode is provided on the silicon substrate and is made of a conductive material with a large work function. Examples of conductive materials with a large work function include nickel, silver, gold, platinum, palladium, selenium, rhodium, ruthenium, iridium, rhenium, tungsten, molybdenum, chromium, tantalum, niobium, alloys thereof, tin oxide (SnO), indium tin oxide (ITO), zinc oxide, and titanium oxide.

The cathode is constructed using a conductive material with a small work function. As such a conductive material, for example, an alloy of an active metal such as Li, Mg, or Ca and a metal such as Ag, Al, or In, or a structure in which these are laminated can be used. Alternatively, a thin compound layer of active metal such as Li, Mg or Ca and halogen such as fluorine or bromine or oxygen may be inserted between the organic layer.

The anode and cathode are patterned into a suitable shape according to the driving method of the display device. For example, when the drive system of the organic EL display device is a simple matrix type, the anode and the cathode are formed in stripes that intersect with each other, and the intersection of these stripes becomes the organic EL element.

The organic layer has at least a white light-emitting layer, and is usually composed of a plurality of layers of organic layers, and may have a charge injection layer such as a hole injection layer or an electron injection layer, or a charge transport layer such as a hole transport layer that transports holes to the white light-emitting layer or an electron transport layer that transports electrons to the white light-emitting layer.

A known layer can be used as long as it can emit white light. Emission characteristics of white color should include emission in at least three regions of red region (600 nm to 780 nm), green region (475 nm to 600 nm), and blue region (380 nm to 475 nm). The number of emission peaks does not necessarily need to be three or more. For example, two emission peaks may be used as long as they emit light in the above region. However, in order to obtain wide color reproducibility, it is preferable to use a white light-emitting layer having three or more emission peaks, and one or more of the above three color regions preferably has an emission peak.

A material constituting such a white light-emitting layer is not particularly limited as long as it emits fluorescence or phosphorescence. Moreover, the light-emitting material may have a hole-transport property or an electron-transport property. Examples of light-emitting materials include dye-based materials, metal complex-based materials, and polymer-based materials.

Examples of the dye-based material include cyclopentamine derivatives, tetraphenylbutadiene derivatives, triphenylamine derivatives, oxadiazole derivatives, pyrazoloquinoline derivatives, distyrylbenzene derivatives, distyrylarylene derivatives, silole derivatives, thiophene ring compounds, pyridine ring compounds, perinone derivatives, perylene derivatives, oligothiophene derivatives, trifmanylamine derivatives, oxadiazole dimers, and pyrazoline dimers.

Examples of the above-mentioned metal complex materials include aluminum quinolinol complexes, benzoquinolinol beryllium complexes, benzoxazole zinc complexes, benzothiazole zinc complexes, azomethyl zinc complexes, porphyrin zinc complexes, and europium complexes, or metal complexes having a central metal such as Al, Zn, Be, etc. or a rare earth metal such as Tb, Eu, Dy, and a ligand having an oxadiazole, thiadiazole, phenylpyridine, phenylbenzimidazole, quinoline structure, or the like. can be mentioned.

Examples of the polymer material include polyparaphenylene vinylene derivatives, polythiophene derivatives, polyparaphenylene derivatives, polysilane derivatives, polyacetylene derivatives, polyfluorene derivatives, polyvinylcarbazole derivatives, and polymers obtained by polymerizing the above dye materials and metal complex materials.

Examples of the method for forming the white light-emitting layer include a vapor deposition method, a printing method, an inkjet method, a spin coating method, a casting method, a dipping method, a bar coating method, a blade coating method, a roll coating method, a gravure coating method, a flexographic printing method, a spray coating method, and a self-assembly method (alternate adsorption method, self-assembled monolayer method). In particular, vapor deposition, spin coating, and inkjet are preferably used, and the film thickness of the white light-emitting layer is usually about 5 nm to 5 μm.

Further, the organic EL layer may have a hole injection layer formed between the white light emitting layer and the anode. This is because the provision of the hole-injection layer stabilizes the injection of holes into the white light-emitting layer, which can increase the light emission efficiency. As a material for forming the hole injection layer, a material generally used for the hole injection layer of an organic EL device can be used. Further, the material for forming the hole injection layer may be any material that has either hole injection properties or electron barrier properties.

Specific examples of materials for forming the hole injection layer include conductive polymer oligomers such as triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, polysilane-based, aniline-based copolymers, and thiophene oligomers.

Furthermore, examples of materials for forming the hole injection layer include porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds. The film thickness of the hole injection layer is usually about 5 nm to 1 μm.

Further, the organic EL layer may have an electron injection layer formed between the white light emitting layer and the cathode. By providing the electron injection layer, the injection of electrons into the white light emitting layer can be stabilized and the luminous efficiency can be improved.

Materials for forming the electron injection layer include, for example, nitro-substituted fluorene derivatives, anthraquinodimethane derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, heterocyclic tetracarboxylic acid anhydrides such as naphthaleneperylene, carbodiimides, frelenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives, thiazole derivatives in which the oxygen atom of the oxadiazole ring of the oxadiazole derivative is substituted with a sulfur atom, and a quinoxaline ring known as an electron-withdrawing group. quinoxaline derivatives, metal complexes of 8-quinolinol derivatives such as tris(8-quinolinol)aluminum, phthalocyanines, metal phthalocyanines, and distyrylpyrazine derivatives.

The present invention will now be described with reference to examples. "Parts" and "%" in the examples represent "parts by mass" and "% by mass", respectively.

First, prior to Examples, methods for producing a resin-type dispersant, a binder resin solution, a colorant, a pigment dispersion, and a photosensitive coloring composition will be described. Moreover, the method for measuring the weight average molecular weight (Mw) and acid value of the resin is as follows.

(Weight average molecular weight)
The weight-average molecular weight (Mw) of the resin is measured using a TSKgel column (manufactured by Tosoh Corporation) with a GPC (manufactured by Tosoh Corporation, HLC-8320GPC) equipped with an RI detector, using THF as a developing solvent.

(acid value)
The resin acid value is a value obtained by converting the measured acid value (mgKOH/g) into solid content based on the potentiometric titration method of JIS K 0070.

<Production of resin type dispersant solution>
(Resin-type dispersant solution 1): Photosensitive resin A reaction vessel equipped with a gas inlet tube, a thermometer, a condenser, and a stirrer was charged with 8 parts of 3-mercapto-1,2-propanediol, 12 parts of pyromellitic anhydride, 80 parts of propylene glycol monomethyl ether acetate (PGMAc), and 0.2 parts of monobutyltin oxide as a catalyst. It was confirmed by acid value measurement that 95% or more of the acid anhydride was half-esterified. Next, 15 parts of methyl methacrylate (MMA), 10 parts of t-butyl acrylate (tBA), 10 parts of ethyl acrylate (EA), 5 parts of methacrylic acid (MAA), 10 parts of benzyl methacrylate (BzMA), and 50 parts of 2-hydroxyethyl methacrylate (HEMA) were charged, the inside of the reaction vessel was heated to 80° C., 1 part of 2,2′-azobis(2,4-dimethylvaleronitrile) was added and reacted for 12 hours. (Second step). Solid content measurement confirmed that 95% had reacted. Next, the inside of the flask was replaced with air, 54.0 parts of 2-methacryloyloxyethyl isocyanate (MOI) and 0.1 part of hydroquinone were charged, and the reaction was carried out at 70° C. for 4 hours (third step). After confirming the disappearance of the peak at 2270 cm ⁻¹ based on the isocyanate group by IR, the reaction solution was cooled and the solid content was adjusted with PGMAc to obtain a resin-type dispersant solution 1 which is a photosensitive resin having a solid content of 40%. The obtained resin type dispersant had an acid value of 36 and a weight average molecular weight of 12,000.

(Resin type dispersant solution 2): Non-photosensitive 30 parts of ethyl acrylate, 20 parts of tert-butyl acrylate, and 40 parts of 2-methyl methacrylate were introduced into a reaction vessel equipped with a non-photosensitive gas inlet tube, a thermometer, a condenser and a stirrer, and the mixture was purged with nitrogen gas. The inside of the reaction vessel was heated to 80° C., and a solution obtained by dissolving 0.1 part of 2,2′-azobisisobutyronitrile in 45.7 parts of cyclohexanone was added to 6 parts of 3-mercapto-1,2-propanediol, and reacted for 10 hours. Solid content measurement confirmed that 95% had reacted. At this time, the weight average molecular weight was 4,000. Next, 9.7 parts of pyromellitic dianhydride, 70 parts of PGMAc, and 0.20 parts of 1,8-diazabicyclo-[5.4.0]-7-undecene as a catalyst were added and reacted at 120° C. for 7 hours. It was confirmed by acid value measurement that 98% or more of the acid anhydride was half-esterified, and the reaction was terminated. After completion of the reaction, the non-volatile content was adjusted to 40% by mass, and a PGMAc solution of a resin type dispersant (resin type dispersant solution 2) having a weight average molecular weight of 8,100, an acid value of 50 mgKOH/g, and a glass transition temperature of the vinyl polymerization site of 22.5°C was obtained.

<Production of binder resin>
(Acrylic resin solution 1): Photosensitive resin 100 parts of propylene glycol monomethyl ether acetate was placed in a reaction vessel equipped with a separable four-necked flask equipped with a thermometer, a cooling tube, a nitrogen gas inlet tube, and a stirrer. The vessel was heated to 120°C while injecting nitrogen gas. was added dropwise over 2.5 hours to carry out a polymerization reaction. Next, the inside of the flask was replaced with air, 0.3 parts of trisdimethylaminomethylphenol and 0.3 parts of hydroquinone were added to 17.0 parts of acrylic acid, and the reaction was continued for 5 hours at 120°C.
Further, 30.4 parts of tetrahydrophthalic anhydride and 0.5 parts of triethylamine were added and allowed to react at 120° C. for 4 hours.

(Acrylic resin solution 2): Photosensitive resin Into a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel and a nitrogen introduction tube, 182 g of propylene glycol monomethyl ether acetate was introduced. FA-513M) 22.0 g (0.10 mol) and propylene glycol monomethyl ether acetate 136 g to which 3.6 g of azobisisobutyronitrile was added was added dropwise to the flask over 2 hours, followed by stirring at 100° C. for 5 hours. Next, the atmosphere in the flask was changed from nitrogen to air, 35.5 g [0.25 mol, (50 mol% with respect to the carboxyl group of methacrylic acid used in this reaction)] of glycidyl methacrylate, 0.9 g of trisdimethylaminomethylphenol, and 0.145 g of hydroquinone were charged into the flask, the reaction was continued at 110°C for 6 hours, and propylene glycol monomethyl ether acetate was added so that the nonvolatile content was 20%, and the solid content acid value was 79 mgKOH/g. of acrylic resin solution 2 was obtained. The polystyrene equivalent weight average molecular weight measured by GPC was 13,000, and the molecular weight distribution (Mw/Mn) was 2.1.

(Acrylic resin solution 3): A reaction vessel equipped with a non-photosensitive separable 4-necked flask, a thermometer, a cooling tube, a nitrogen gas inlet tube, a dropping tube and a stirring device was charged with 196 parts of cyclohexanone. A mixture of 20.7 parts of oxide-modified acrylate ("Aronix M110" manufactured by Toagosei Co., Ltd.) and 1.1 parts of 2,2'-azobisisobutyronitrile was added dropwise over 2 hours. After completion of dropping, the reaction was continued for 3 more hours to obtain an acrylic resin solution.
After cooling to room temperature, about 2 parts of the resin solution was sampled and dried by heating at 180 ° C. for 20 minutes to measure the nonvolatile content. The weight average molecular weight (Mw) was 26,000.

<Production of colorant (A)>
(Micronized red pigment (PR254-1))
Diketopyrrolopyrrole red pigment C.I. I. Pigment Red 254 ("Irgajin RedL 3630" manufactured by BASF) (200 parts), sodium chloride (1400 parts) and diethylene glycol (360 parts) were placed in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 80°C for 6 hours. Next, this kneaded product was put into 8000 parts of hot water, stirred for 2 hours while heating to 80 ° C. to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and dried at 85 ° C. for a whole day and night to obtain a diketopyrrolopyrrole-based fine red pigment (PR254-1).

(Micronized yellow pigment (PY139-1))
yellow pigment C.I. I. 200 parts of Pigment Yellow 139 (“Pariotol Yellow D1819” manufactured by BASF), 1400 parts of sodium chloride and 360 parts of diethylene glycol were placed in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 80° C. for 6 hours. Next, this kneaded product was put into 8000 parts of hot water, stirred for 2 hours while heating to 80 ° C. to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and dried at 85 ° C. overnight to obtain a finely divided yellow pigment (PY139-1).

(Micronized yellow pigment (PY185-1))
As a yellow colorant, C.I. I. Pigment Yellow 185 (BASF "Paliotol Yellow L 1155") 200 parts, sodium chloride 1000 parts and diethylene glycol 100 parts were placed in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 100° C. for 6 hours. Next, this kneaded product was put into 5 liters of warm water, stirred for 1 hour while heating to 70 ° C. to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight to obtain a finely divided yellow pigment (PY185-1).

(Micronized green pigment (PG58-1))
phthalocyanine green pigment C.I. I. 200 parts of Pigment Green 58 ("FASTOGEN GREEN A110" manufactured by DIC Corporation), 1400 parts of sodium chloride and 360 parts of diethylene glycol were placed in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 80°C for 6 hours. Next, this kneaded product was put into 8000 parts of hot water, stirred for 2 hours while heating to 80 ° C. to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 85 ° C. for a whole day and night to obtain a phthalocyanine-based fine green pigment (PG58-1).

(Micronized blue pigment (PB15:6-1))
phthalocyanine blue pigment C.I. I. Pigment Blue 15:6 (“LIONOL BLUE ES” manufactured by Toyocolor Co., Ltd., specific surface area 60 m ² /g) 200 parts, sodium chloride 1400 parts, and diethylene glycol 360 parts were placed in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 80° C. for 6 hours. Next, this kneaded product was put into 8000 parts of hot water, stirred for 2 hours while heating to 80° C. to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and dried at 85° C. for a whole day and night to obtain a finely divided phthalocyanine blue pigment (PB15:6-1).

(Micronized blue pigment (PB15:3-1))
200 parts of phthalocyanine blue pigment (CI Pigment Blue 15:3, "LIONOL BLUE FG-7351" manufactured by Toyocolor Co., Ltd.), 600 parts of sodium chloride, and 600 parts of diethylene glycol were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 120 ° C. for 8 hours. Next, this kneaded product was put into 5 liters of hot water and stirred for 1 hour while heating to 70° C. to form a slurry, which was repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80° C. for a whole day and night to obtain a finely divided phthalocyanine blue pigment (PB15:3-1).

(Micronized purple pigment (PV23-1))
dioxazine-based purple pigment C.I. I. Pigment Violet 23 (“LIONOGEN VIOLET RL” manufactured by Toyocolor Co., Ltd.) 200 parts, sodium chloride 1400 parts, and diethylene glycol 360 parts were placed in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 80° C. for 6 hours. Next, this kneaded product was put into 8000 parts of hot water, stirred for 2 hours while heating to 80° C. to form a slurry, filtered and washed repeatedly with water to remove sodium chloride and diethylene glycol, and dried at 85° C. for a whole day and night to obtain a dioxazine-based finely divided purple pigment (PV23-1).

<Method for producing salt-forming compound (V)>
The C.I. I. A salt-forming compound (V) was prepared from Acid Red 289 and a quaternary ammonium salt compound, tristearylmonomethylammonium chloride. C.I. I. After dissolving 10 parts of Acid Red 289 in 200 parts of water and heating to 30 to 50° C., 5.5 parts of tristearylmonomethylammonium chloride was dissolved in a 20/80 solution of methanol/water to give a 5% solution, and added dropwise. After dropping the tristearylmonomethylammonium chloride solution, the mixture was stirred at 30 to 50° C. for 3 hours. After allowing to cool to room temperature while stirring, suction filtration is performed, and after washing with water, the salt-forming compound remaining on the filter paper is dried by removing moisture with a dryer. I. 8 parts of a salt-forming compound (V) of Acid Red 289 and tristearylmonomethylammonium chloride was obtained.

<Production of pigment dispersion>
(Pigment dispersion (PR-1))
After stirring and mixing the following mixture uniformly, zirconia beads with a diameter of 0.5 mm were used to disperse for 3 hours with an Eiger mill ("Mini Model M-250 MKII" manufactured by Eiger Japan), and then filtered through a 5.0 μm filter to prepare a pigment dispersion (PR-1) having a nonvolatile content of 20% by mass.
Fine red pigment (PR254-1): 14.8 parts Acrylic resin solution 3: 6.0 parts Propylene glycol monomethyl ether acetate: 69.2 parts Resin type dispersant solution 1 (photosensitive resin): 10.0 parts

(Pigment dispersion (PR-2))
After stirring and mixing the following mixture uniformly, zirconia beads with a diameter of 0.5 mm were used to disperse for 3 hours with an Eiger mill ("Mini Model M-250 MKII" manufactured by Eiger Japan Co., Ltd.), and then filtered through a 5.0 μm filter to prepare a pigment dispersion (PR-2) having a nonvolatile content of 20% by mass.
Fine red pigment (PR254-1): 14.8 parts Acrylic resin solution 3: 6.0 parts Propylene glycol monomethyl ether acetate: 69.0 parts Resin type dispersant solution 2: 10.0 parts

(Pigment dispersion (PY-1))
After stirring and mixing the following mixture uniformly, using zirconia beads with a diameter of 0.5 mm, after dispersing for 3 hours with an Eiger mill ("Mini Model M-250 MKII" manufactured by Eiger Japan), a 5.0 μm filter was used to prepare a pigment dispersion (PY-1) having a nonvolatile content of 20% by mass.
Fine yellow pigment (PY139-1): 14.0 parts Acrylic resin solution 3: 8.0 parts Propylene glycol monomethyl ether acetate: 67.0 parts Resin type dispersant solution 1 (photosensitive resin): 11.0 parts

(Pigment dispersion (PY-2))
After stirring and mixing the following mixture uniformly, zirconia beads with a diameter of 0.5 mm were used to disperse for 3 hours with an Eiger mill ("Mini Model M-250 MKII" manufactured by Eiger Japan Co., Ltd.), and then filtered through a 5.0 μm filter to prepare a pigment dispersion (PY-2) having a nonvolatile content of 20% by mass.
Fine yellow pigment (PY139-1): 14.0 parts Acrylic resin solution 3: 8.0 parts Propylene glycol monomethyl ether acetate: 67.0 parts Resin type dispersant solution 2: 11.0 parts

(Pigment dispersion (PY-3))
After stirring and mixing the following mixture uniformly, zirconia beads with a diameter of 0.5 mm were used to disperse for 3 hours with an Eiger mill ("Mini Model M-250 MKII" manufactured by Eiger Japan), and then filtered through a 5.0 μm filter to prepare a pigment dispersion (PY-3) having a nonvolatile content of 20% by mass.
Fine yellow pigment (PY185-1): 14.0 parts Acrylic resin solution 3: 8.0 parts Propylene glycol monomethyl ether acetate: 67.0 parts Resin type dispersant solution 1 (photosensitive resin): 11.0 parts

(Pigment dispersion (PY-4))
After stirring and mixing the following mixture uniformly, zirconia beads with a diameter of 0.5 mm were used to disperse for 3 hours with an Eiger mill (manufactured by Eiger Japan Co., Ltd. "Mini Model M-250 MKII"), and then filtered through a 5.0 μm filter to prepare a pigment dispersion (PY-4) having a nonvolatile content of 20% by mass.
Fine yellow pigment (PY185-1): 14.0 parts Acrylic resin solution 3: 8.0 parts Propylene glycol monomethyl ether acetate: 67.0 parts Resin type dispersant solution 2: 11.0 parts

(Pigment dispersion (PG-1))
After stirring and mixing the following mixture uniformly, zirconia beads with a diameter of 0.5 mm were used to disperse for 3 hours with an Eiger mill (manufactured by Eiger Japan Co., Ltd. "Mini Model M-250 MKII"), and then filtered through a 5.0 μm filter to prepare a pigment dispersion (PG-1) having a nonvolatile content of 20% by mass.
Micronized green pigment (PG58-1): 13.0 parts Acrylic resin solution 3: 11.0 parts Propylene glycol monomethyl ether acetate: 52.0 parts Resin type dispersant solution 1 (photosensitive resin): 64.0 parts

(Pigment dispersion (PG-2))
After stirring and mixing the following mixture uniformly, zirconia beads with a diameter of 0.5 mm were used to disperse for 3 hours with an Eiger mill (manufactured by Eiger Japan Co., Ltd. "Mini Model M-250 MKII"), and then filtered through a 5.0 μm filter to prepare a pigment dispersion (PG-2) having a nonvolatile content of 20% by mass.
Micronized green pigment (PG58-1): 13.0 parts Acrylic resin solution 3: 11.0 parts Propylene glycol monomethyl ether acetate: 64.0 parts Resin type dispersant solution 2: 12.0 parts

(Pigment Dispersion (PB-1))
After stirring and mixing the following mixture uniformly, zirconia beads with a diameter of 0.5 mm were used to disperse for 3 hours with an Eiger mill (manufactured by Eiger Japan Co., Ltd. "Mini Model M-250 MKII"), and then filtered through a 5.0 μm filter to prepare a pigment dispersion (PB-1) having a nonvolatile content of 20% by mass.
Micronized blue pigment (PB15: 6-1): 14.0 parts Acrylic resin solution 3: 8.0 parts Propylene glycol monomethyl ether acetate: 67.0 parts Resin type dispersant solution 1 (photosensitive resin): 11.0 parts

(Pigment dispersion (PB-2))
After stirring and mixing the following mixture uniformly, zirconia beads with a diameter of 0.5 mm were used to disperse for 3 hours with an Eiger mill (manufactured by Eiger Japan Co., Ltd. "Mini Model M-250 MKII"), and then filtered through a 5.0 μm filter to prepare a pigment dispersion (PB-2) having a nonvolatile content of 20% by mass.
Micronized blue pigment (PB15: 6-1): 14.0 parts Acrylic resin solution 3: 8.0 parts Propylene glycol monomethyl ether acetate: 67.0 parts Resin type dispersant solution 2: 11.0 parts

(Pigment dispersion (PB-3))
After stirring and mixing the following mixture uniformly, zirconia beads with a diameter of 0.5 mm were used to disperse for 3 hours with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan), and then filtered through a 5.0 μm filter to prepare a pigment dispersion (PB-3) having a nonvolatile content of 20% by mass.
Micronized blue pigment (PB15: 3-1): 13.0 parts Acrylic resin solution 3: 16.0 parts Propylene glycol monomethyl ether acetate: 61.0 parts Resin type dispersant solution 1 (photosensitive resin): 10.0 parts

(Pigment dispersion (PB-4))
After stirring and mixing the following mixture uniformly, zirconia beads with a diameter of 0.5 mm were used to disperse for 3 hours with an Eiger mill (manufactured by Eiger Japan Co., Ltd. "Mini Model M-250 MKII"), and then filtered through a 5.0 μm filter to prepare a pigment dispersion (PB-4) having a nonvolatile content of 20% by mass.
Micronized blue pigment (PB15: 3-1): 13.0 parts Acrylic resin solution 3: 16.0 parts Propylene glycol monomethyl ether acetate: 61.0 parts Resin type dispersant solution 2: 10.0 parts

(Pigment Dispersion (PV-1))
After stirring and mixing the following mixture uniformly, zirconia beads with a diameter of 0.5 mm were used to disperse for 3 hours with an Eiger mill (manufactured by Eiger Japan Co., Ltd. "Mini Model M-250 MKII"), and then filtered through a 5.0 μm filter to prepare a pigment dispersion (PV-1) having a nonvolatile content of 20% by mass.
Fine purple pigment (PV23-1): 10.0 parts Acrylic resin solution 3: 14.0 parts Propylene glycol monomethyl ether acetate: 58.0 parts Resin type dispersant solution 1 (photosensitive resin): 18.0 parts

(Pigment dispersion (PV-2))
After stirring and mixing the following mixture uniformly, zirconia beads with a diameter of 0.5 mm were used to disperse for 3 hours with an Eiger mill (manufactured by Eiger Japan Co., Ltd. "Mini Model M-250 MKII"), and then filtered through a 5.0 μm filter to prepare a pigment dispersion (PV-2) having a nonvolatile content of 20% by mass.
Micronized purple pigment (PV23-1): 10.0 parts Acrylic resin solution 3: 14.0 parts Propylene glycol monomethyl ether acetate: 58.0 parts Resin type dispersant solution 2: 18.0 parts

<Method for producing salt-forming compound-containing resin solution (SV)>
After stirring and mixing the following mixture so as to be uniform, the mixture was filtered through a 5.0 μm filter to prepare a salt-forming compound-containing resin solution (SV).
Salt-forming compound (V): 13.00 parts Cyclohexanone: 87.00 parts

<Production of photosensitive coloring composition>
[Production Example 1]
(Photosensitive coloring composition (R-1))
The following mixture was uniformly stirred and mixed, and then filtered through a 1.0 μm filter to obtain a photosensitive coloring composition (R-1).
Pigment dispersion (PR-1): 58.2 parts Pigment dispersion (PY-1): 17.4 parts Trimethylolpropane triacrylate: 3.8 parts ("Aronix M-309" manufactured by Toagosei Co., Ltd.)
Dipentaerythritol hexaacrylate: 3.8 parts ("Aronix M-402" manufactured by Toagosei Co., Ltd.)
Photopolymerization initiator (manufactured by BASF "OXE-02"): 0.7 parts Propylene glycol monomethyl ether acetate: 16.0 parts

[Production Examples 2 to 47]
(Preparation of photosensitive coloring composition (R-2 to 47))
Pigment dispersion, a photopolymerizable monomer, a photopolymerization initiator, and a photosensitive coloring composition (R-1) except that the type and amount of the acrylic resin solution were changed to the contents shown in Tables 1 to 3. A photosensitive coloring composition (R-2 to 47) was obtained in the same manner.

The abbreviations in Table 1-3 are shown below.
<Photopolymerizable monomer (B)>
Photopolymerizable monomer B-1: trimethylolpropane triacrylate ("Aronix M-309" manufactured by Toagosei Co., Ltd.)
Photopolymerizable monomer B-2: trimethylolpropane PO-modified triacrylate (manufactured by Toagosei Co., Ltd. "Aronix M-350)
Photopolymerizable monomer B-3: dipentaerythritol hexaacrylate ("Aronix M-402" manufactured by Toagosei Co., Ltd.)
<Photoinitiator (C)>
Photopolymerization initiator C-1: ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(O-acetyloxime)
("IRGACURE OXE 02" manufactured by BASF)
Photoinitiator C-2: 1.2-octanedione, 1-[4-(phenylthio)-, 2-(O-benzoyloxime)]
(“IRGACURE OXE 01” manufactured by BASF)
Photopolymerization initiator C-3: a compound represented by the following chemical formula

Photoinitiator C-4: 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1
("IRGACURE 369E" manufactured by BASF)

<Manufacture of OLED element>
A TFT layer was formed on a silicon substrate using a known method such as a sputtering method or an etching method. Furthermore, after forming a white organic EL element on the TFT layer by using a known method such as vapor deposition, silicon nitride was coated by a CVD method to form an organic EL element substrate.

<Manufacturing of color filters and organic EL display devices>
On the OLED element, a green photosensitive resin composition was applied with a spinner so that the film thickness of the cured finish was 1.5 μm, and the green layer (G) of the color filter was formed through the steps of ultraviolet exposure, alkali development, water washing and drying through a pattern mask. After that, it was cured by heating at 80° C. for 10 minutes using a heating oven to complete the formation of the green layer (G) of the color filter.

Next, in the same manner as the method for forming the green layer (G) of the color filter described above, the red photosensitive resin composition was applied with a spinner so that the film thickness of the cured finish was 1.5 μm, and the green layer (R) of the color filter was temporarily formed through the steps of ultraviolet exposure, alkali development, water washing and drying through a pattern mask. Then, it was cured by heating at 80° C. for 10 minutes using a heating oven to complete the formation of the red layer (R) of the color filter.

Furthermore, in the same manner as the method for forming the green layer (G) of the color filter described above, the blue photosensitive resin composition was applied with a spinner so that the film thickness of the cured finish was 1.5 μm, and the blue layer (B) of the color filter was temporarily formed through the steps of ultraviolet exposure, alkali development, water washing and drying through a pattern mask. Thereafter, the composition was cured by heating at 80° C. for 10 minutes using a heating oven to complete the formation of the blue layer (B) of the color filter, thereby producing a color filter.

After forming green, red, and blue layers, they were bonded to a cover glass using a sealant Structbond XMF-T107 (manufactured by Mitsui Chemicals, Inc.) to produce an organic EL display device.

Table 4 shows the photosensitive coloring composition used in the production of the color filter and the organic EL display device.

Table 5 shows the results of measuring the appearance and spectral transmittance of the color filters and organic EL display devices of Examples 1 to 14 and Comparative Examples 1 to 3.

<Appearance Observation of Color Filter and Organic EL Display Device>
Appearance observation was carried out by reflection observation with an optical microscope "ECLIPSE LV100" manufactured by NIKON. A case where there was no pixel penetration or surface roughness was evaluated as ⊚, a case where slight penetration was observed as Δ, and a case where surface roughness was observed as color penetration from adjacent pixels was evaluated as ×. It was determined that the surface roughness and color bleeding from adjacent pixels were not practical.
In addition, as evaluation of pixel overlap, the case where the amount of overlap of red, green, and blue pixels was less than 0.1 μm was evaluated as ◯, the case where the amount of pixel overlap was 0.1 μm or more and less than 0.3 μm was evaluated as Δ, and the case of 0.3 μm or more was evaluated as ×. If the pixel overlap amount is 0.3 μm or more, the display area becomes small, which causes a reduction in the luminance of the organic EL display device, and is therefore judged to be impractical.

<Chromaticity of organic EL display device>
Chromaticity during red display, green display, and blue display in the organic EL display devices of Examples 1 to 14 and Comparative Examples 1 to 3 was measured using a "spectral radiance meter CS-1000" manufactured by Olympus. The NTSC area ratio (the ratio of the color gamut of the organic EL display device of Example or Comparative Example to the color gamut defined by the NTSC standard) was calculated from the obtained chromaticities of red, green, and blue.
Those with an NTSC area ratio of 85% or more were evaluated as ◯, and those with an NTSC area ratio of less than 85% were evaluated as x. If the NTSC area ratio is less than 85%, the image will appear to lack sharpness when displayed as an organic EL display device, so it was judged not to be practical.
^All pixels of red, green, and blue are lit and ^displayed , and the luminance ⁽ WL) when ^{white is displayed is 330 cd/m 2 or more} . If the luminance is less than 280 cd/m ² , the image will appear dark when displayed, so it was determined that this is not practical as an organic EL display device.

<Spectral characteristic evaluation>
Green, red, and blue color filters were formed on glass substrates having a thickness of 1.1 mm in the same manner as in the method for forming the color filters described above. In addition, green, red, and blue color filters were formed on glass substrates having a thickness of 1.1 mm in the same manner as the above method for forming color filters, except that the firing temperature was changed to 200°C. Then, the spectral transmittance shown in Table 6 was measured with a microscopic spectrophotometer ("OSP-SP200" manufactured by Olympus Optical Co., Ltd.). Table 6 shows the results. In addition, as spectral characteristics, with respect to the maximum spectral transmittance measured in the state of only red pixels, only green pixels, and only blue pixels, the spectral changes of the color filters produced in Examples and Comparative Examples were evaluated by ⊚ when the change was within 1%, ○ when within 3%, Δ when within 5%, and X when greater than 5%. If the spectral change is greater than 5%, the coloring material of the pixels adjacent to the pixel to be spectroscopically measured permeates, and the transmittance becomes unstable in the plane of the substrate.

From the results in Table 6, when the color filter is formed by baking at 80° C., the spectral transmittance of the red pixels is 0.4% or less for light in the wavelength range of 450 nm to 560 nm, and the maximum transmittance for light in the range of 600 nm to 700 nm is 80% or more and less than 100%. is 70% or more, and the transmittance of light at 550 nm is 60% or less, the spectral transmittance of the blue pixel is less than 20% in the wavelength range of 500 nm to 560 nm, and the red, green, and blue pixels are formed. Got.
On the other hand, in the case of firing at 200 ° C., unlike the case of firing at 80 ° C., the problem of deterioration of spectral characteristics is improved even at the level where it was observed. Therefore, it can be said that it is possible to provide a high-quality color filter even when firing at a low temperature when using the red, green, and blue colored compositions that correspond to the present invention.

When the results in Tables 5 and 6 are integrated, the content of the compound represented by the general formula (1) in the photosensitive coloring composition used to form the red, green, and blue pixels is 50% by mass or more with respect to the total amount of photopolymerizable monomers.
On the other hand, when the compound represented by the general formula (1) is not used, the pixel size becomes too large when the exposure is performed to the extent that no appearance defect occurs, and the red, green, and blue pixels overlap, resulting in a decrease in luminance and a decrease in the quality of the organic EL display device.

In the photosensitive coloring composition used to form the red, green, and blue pixels, when the compound represented by the general formula (2) was used as the oxime ester photopolymerization initiator, the surface roughness of the red, green, and blue pixels did not occur even in baking at a low temperature of 80 ° C., and a color filter and an organic EL display device with higher brightness and a wider color gamut were obtained.

INDUSTRIAL APPLICABILITY The present invention can be used as an organic EL display device for electronic devices such as smart glasses, head-mounted displays, and electronic viewfinders.

1 silicon wafer 2 organic EL layer 3 color filter 4 sealing layer 5 cover glass 10 organic EL display devices 3a, 3b, 3c pixels

Claims (6)

An organic EL display device having an organic EL layer and a color filter on a silicon substrate on which driving elements are formed,
the color filter has pixels including red pixels, green pixels, and blue pixels;
The film thickness of the pixel is in the range of 1.0 μm to 2.0 μm,
In the spectral transmittance of the red pixel, the maximum transmittance of light in the wavelength range of 450 nm to 560 nm is 0.4% or less, and the transmittance of light in the wavelength range of 600 nm to 700 nm is 80% or more and less than 100%;
The spectral transmittance of the green pixel has a maximum transmittance of 2% or less for light in the wavelength range of 400 nm to 470 nm, a transmittance of 70% or more for light with a wavelength of 520 nm, and a transmittance of 60% or less for light with a wavelength of 550 nm,
The spectral transmittance of the blue pixel has a maximum light transmittance of less than 20% in a wavelength range of 500 nm to 560 nm,
The pixel contains a coloring agent (A), a photopolymerizable monomer (B), a photopolymerization initiator (C), and a resin (D), and the photopolymerization monomer (B) is the following general formula (1).
General formula (1)
[ _CH2 =CHC(=O)-( _OCmH2m ) _{n -OCH2 ] 3 - CCH2CH3}
(In general formula (1), m represents an integer of 1 to 3, n represents an integer of 0 to 2, and multiple m and n may be the same or different.) 2. The organic EL display device according to claim 1, wherein the content of the compound represented by formula (1) is 50% by mass or more relative to the total amount of the photopolymerizable monomer (B). 3. The organic EL display device according to claim 1, wherein the oxime ester photopolymerization initiator is a compound represented by the following general formula (2).

(In general formula (2), Z represents a direct bond or a -C(=O)- group, R ¹ represents an optionally substituted C 1-20 alkyl group, R ² represents an optionally substituted C 1-20 alkyl group, or an optionally substituted aryl group, and R ³ to R ¹⁰ each independently represents a hydrogen atom, an optionally substituted C 1-20 alkyl group, an optionally substituted aryl group, or a nitro group. , or represents an R ¹¹ -C(=O)- group.R ¹¹ represents an aryl group which may have a substituent.) The organic EL display device according to any one of claims 1 to 3, wherein the resin (D) contains a photosensitive resin. The photosensitive resin is
In the presence of the reaction product of the hydroxyl group of the compound (a) having two hydroxyl groups and one thiol group in the molecule and the acid anhydride group of pyromellitic anhydride and/or trimellitic anhydride, the hydroxyl group of a hydroxyl group-containing polymer obtained by polymerizing the ethylenically unsaturated monomer (c) containing the hydroxyl group-containing ethylenically unsaturated monomer (b), and the compound (d) having one isocyanate group and one or more (meth)acryloyl groups. Is a resin reacted with an isocyanate group,
The content of structural units derived from the hydroxyl group-containing ethylenically unsaturated monomer (b) is 35% by mass or more and 80% by mass or less relative to the total amount of structural units derived from the ethylenically unsaturated monomer (c). The organic EL display device according to claim 4, comprising a photosensitive resin (E). the content of the coloring agent (A) in the red pixel is 24% by mass or more and 67% by mass or less;
The content of the coloring agent (A) in the green pixel is 30% by mass or more and 55% by mass or less, and
6. The organic EL display device according to claim 1, wherein the content of the coloring agent (A) in said blue pixels is 30% by mass or more and 47% by mass or less.

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